Submitted by Celso Magalhaes (celsomagalhaes@ufrrj.br) on 2017-05-09T14:28:22Z
No. of bitstreams: 1
2016 - Leonardo Santos de Barros.pdf: 6766023 bytes, checksum: 16ce8cf6e87d3cfab0a3d73fc9a6e46c (MD5) / Made available in DSpace on 2017-05-09T14:28:22Z (GMT). No. of bitstreams: 1
2016 - Leonardo Santos de Barros.pdf: 6766023 bytes, checksum: 16ce8cf6e87d3cfab0a3d73fc9a6e46c (MD5)
Previous issue date: 2016-11-19 / Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior - CAPES / The photochemical reactivity of chalcone (CH) nanocrystals and its fluorinated derivatives (CH4F, CH23F, CH25F, CH26F, CH34F, CH35F, PFCB and the DFC) in a suspension of aqueous CTAB (0.04 mM) was studied by ultraviolet spectroscopy (UV), hydrogen nuclear magnetic resonance (H1NMR) and dynamic light scattering (DLS). The suspension of chalcone nanocrystals was prepared by the reprecipitation method in an aqueous solution of CTAB. The ultraviolet spectrum for the chalcone nanocrystals prior to irradiation showed hypochromic and bathochromic effects when compared to the methanolic solution. The DLS spectrum for CH CH23F, CH25F, CH26F and PFCB nanocrystals in aqueous CTAB showed a polydispersed system containing three different particle sizes, whereas CH34F, CH35F and DFC nanocrystals showed a clear monodispersivity. After irradiation, the DLS spectrum for these nanocrystals did not show significant changes, however for the monodispersed chalcones a shift towards larger particle sizes was observed. After irradiation the UV spectrum for the chalcone nanocrystals indicated a hypochromic effect on the longer wavelength band, which may be related to the consumption of their E-isomer. The kinetic monitoring of the E-isomer consumption for the chalcones CH, CH4F, CH23F, CH25F, CH26F CH34F, CH35F, PFCB and DFC as a function of irradiation time indicated that after a certain time the reaction reaches a steady state, with no more changes on their absorbance. The H1NMR spectrum for the irradiation product of CH4F and CH23F showed the formation of a mixture of ?-, ??-, and ?-truxillic dimers. On the other hand, irradiation of CH25F and CH26F derivatives led to the formation of the ?-truxinic dimer. Photolysis of CH34F and CH35F nanocrystals showed the conversion of the reactant to a cyclobutane through a stereospecific reaction. For CH35F only the ?-truxillic dimer has been formed, in nearly 100% conversion. However, for nanocrystals of the chalcone CH34F the Z-isomer is formed together with the ?-truxillic dimer CH34F, which may be related to a chalcone fraction that was solubilized in the CTAB containing aqueous phase. Irradiation of DFC nanocrystals occurred at a conversion of almost 100% to the cycloaddition product, the ?-truxillic dimer. For chalcone (CH) a high yield formation of the Z-chalcone isomer and dimers that are not formed from its E-isomer was observed, while PFCB appeared as a stable molecule during the irradiation process, and the presence of the five fluorine atoms on the benzyl ring can account for its stability / A reatividade fotoqu?mica de nanocristais de chalcona (CH) e seus derivados fluorados (CH4F, CH23F, CH25F, CH26F, CH34F, CH35F, PFCB e DFC) foi estudada por espectroscopia de ultravioleta (UV), Resson?ncia magn?tica nuclear de hidrog?nio (RMN1H) e Espalhamento de luz din?mico (DLS). A suspens?o dos nanocristais das chalconas foi preparada pelo m?todo de reprecipita??o em uma solu??o aquosa de CTAB. Os espectros no ultravioleta para a suspens?o dos nanocristais das chalconas antes da irradia??o mostraram um efeito hipocr?mico e batocr?mico em rela??o ? solu??o metan?lica. Os espectros de DLS para os nanocristais da suspens?o das chalconas em solu??o aquosa de CTAB se apresentaram como um sistema polidisperso apresentando 3 tamanhos de part?culas para CH, CH23F, CH25F, CH26F, PFCB e monodisperso para CH34F, CH35F e DFC. Ap?s a irradia??o n?o se observou mudan?as significativas na estrutura dos espectros de DLS para os nanocristais, ocorrendo um deslocamento para tamanhos de part?culas maiores nas chalconas monodispersas. O espectro de UV para a suspens?o dos nanocristais das chalconas ap?s a irradia??o indicou um efeito hipocr?mico da banda de maior absor??o, o que pode estar relacionado ao consumo dos compostos de configura??o E.
O acompanhamento cin?tico do consumo do is?mero E das chalconas CH, CH4F, CH23F, CH25F, CH26F CH34F, CH35F, PFCB e DFC contra tempo de irradia??o de uma suspens?o dos nanocristais destas chalconas em solu??o aquosa de CTAB (0,04 mM) indicou que a partir de um determinado tempo a rea??o atinge um estado estacion?rio, n?o apresentando mais mudan?as em sua absorb?ncia. Os espectros de RMN1H para o produto da irradia??o dos nanocristais das chalconas contendo fl?or na posi??o 4 (CH4F) e nas posi??es 2 e 3 (CH23F) mostraram a forma??o de uma mistura de d?meros ?????? e ?-trux?licos. A irradia??o dos derivados CH25F e CH26F levou ? forma??o do d?mero do tipo ?-trux?nico. Para os derivados CH34F e CH35F a convers?o dos reagentes ao fotociclobutano foi feita em uma forma estereoespec?fica, tendo sido formado somente o d?mero ?-trux?lico, com uma convers?o de quase 100% para o CH35F. No entanto, para os nanocristais da chalcona CH34F o is?mero Z-CH34F foi formado juntamente com o d?mero ?-trux?lico, o que pode estar relacionado a fra??es da chalcona que ficaram solubilizadas na fase aquosa contendo CTAB e n?o formaram suspens?o de nanocristais.
A irradia??o dos nanocristais da chalcona DFC ocorreu com uma convers?o de quase 100% ao produto de fotocicloadi??o, sendo o d?mero formado o do tipo ?-trux?lico. Para chalcona (CH) observou-se um elevado rendimento de forma??o do is?mero Z-chalcona e de d?meros que n?o s?o provenientes do is?mero E, enquanto que PFCB apresentou-se como uma mol?cula est?vel durante o processo de irradia??o, com a presen?a dos cinco ?tomos de fl?or no anel benz?lico podendo ser respons?vel pela sua estabilidade
| Identifer | oai:union.ndltd.org:IBICT/oai:localhost:jspui/1607 |
| Date | 19 November 2016 |
| Creators | Barros, Leonardo Santos de |
| Contributors | Ferreira, Jos? Carlos Netto, Cesarin Sobrinho, Dar?, Cavalheiro, Carla Cristina Schmidt, Correia, Rodrigo Jos?, Ferreira, Aur?lio Baird Buarque, Silva, Francisco de Assis da, Garden, Nanci C?mara de Lucas |
| Publisher | Universidade Federal Rural do Rio de Janeiro, Programa de P?s-Gradua??o em Qu?mica, UFRRJ, Brasil, Instituto de Ci?ncias Exatas |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/doctoralThesis |
| Format | application/pdf |
| Source | reponame:Biblioteca Digital de Teses e Dissertações da UFRRJ, instname:Universidade Federal Rural do Rio de Janeiro, instacron:UFRRJ |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 7 REFER?NCIAS BIBLIOGR?FICAS Abdelmoty, I.; Buchholz, V.; Di, Li.; Guo, C.; Kowitz, K.; Enkelmann, V.; Wegner G.; Foxman, B. M. Crystal Growth & Design. (2005), 5(6), 2010-2017. Alias, Y.; Awang, K.; Hadi, A.; Thoison, O.; Sevent, T.; Pais, M., J. Nat. Prod., (1995), 58, 1160. Andrew, D.; Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. (1994), 116, 10870. Arai T.; Karatsu, T.; Tsuchiya, M.; Sakuragi, H.; Tokumaru, K., Chem. Phys. Lett., (1988), 149, 161. Arias-Ruiz, S. N.; Romero, N.; Lobato-Garc?a, C. E.; G?mez-Rivera, A and Mendoza, A. Acta Cryst. (2013). E69, o1694?o1695. Ariel, S.; Askari, S.; Scheffer, 1. R.; Trotter, J.; Walsh, L. J. Am. Chem. Soc. (1984), 106, 5726-5728. Assaid, I.; Bosc, D.; Hardy, I. J. Phys. Chem. B. (2004), 108, 2801-2806. Atkinson, S. D.M.; Almond, M. J.; Hollins, P.; Jenkins, S. L. Spectrochimica Acta Part A 59 (2003) 629-635. Azzaovi, K.; Morin-Allory, L., Chromatographia. (1995), 40, 690. Baba, K.; Kasai, H.; Okada, S.; Oikawa, H.; Nakanishi, H. Opt.Mater. (2003), 21, 591-594. Baba, K.; Nishida, K. Nanoscale Research Letters. (2014), 9, 16. Bart, J. C. J.; Schmidt, G. M. J., Isr. J. Chem. (1971), 9, 429. Bartlett, P.D, Qtr. Rev. (1970), 473. Becker, R. S.; Inuzuka, K.; King, J., J. Chem. Phys., (1970), 52, 5164. Bernstein, J. Conformational Polymorphism. (1987). New York, Elsevier. Bernstein, J. J Phys. D: Appl Phys. (1993), 26, B66-B76 Bernstein, J. Polymorphism and Investigation of Structure-Property Relations in Organic Solids. (1991). Oxford Ford University Press, Oxford, 6-26. Bernstein, J. Polymorphism in Drug Design and Delivery. (1998). Liss, New York, 203-215. 161 Bhandari, P.; Crombie, L.; Daniels, P.; Holden, I.; Vanbruggen, N.; Whiting, Da.; J of Chem.(1992), 7, 849. Biju, V.; Sudeep, P. K.; Thomas, K. G.; George, M. V.; Barazzouk, S.; Kamat, P. V. Langmuir. (2002), 18, 1831-1839. Bilia, A. R.; Morelli; I.; Marsili A., Tetrahedron. (1994), 50, 5181. Blanco, S. E.; Ferretti, F. H., Talanta. (1998), 45, 1103. Bloor, D.; Chance, R. R. Polydiacetylenes; M. Nijhoff: Dordrecht, (1985), 102. Boeck, P.; Falcao, C. A. B.; Leal, P. C., Yunes, R. A.; Cechinel, V.; Torres-Santos, E. C.; Rossi-Bergmann, B.; Biooganic & Medicinal Chem. (2006), 14,1545. Bois, F.; Beney, C.; Boumendjel, A.; Mariotte, A. M.; Conseil, G.; Di Pietro, A., J. Med. Chem. (1998), 41, 4161. Boldyreva, E. V.; Sinelnikov, A. A.; Chupakhin, A. P. ; Lyakhov, N. Z.; Boldyrev, V. V. Doklady Akad. Nauk USSR. (1984), 277, 893?896. Bonneau, R., J. Am. Chem. Soc. (1991), 113, 6245. Bonner, W. C. Top. Stereochem. (1988), 18, 1-98. Bowden, K.; Dalpozzo A. D.; Duah, C. K., J. Chem. Research., (s). (1990), 377. Broeker, J. L.; Eksterowicz, J. E.; Belk, A. J.; Houk, K. N. J. Am. Chem. Soc. (1995), 117, 1847. Bruchez, M., Jr.; Moronne, M.; Gin, P.; Weiss, S. Science. (1998), 281(5385), 2013?2016. Bucar, D. K.; MacGillivray, L. R. J. Am. Chem. Soc. (2007), 129, 32-33. Bucar, Dejan-Kre?imir, Hamilton, T. D. MacGillivray, L. R. Organic Nanostructures. (2008) WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. B?chi, G.; Goldman, I. M., J. Am. Chem. Soc. (1957), 49, 4741. Budde, K.; Quella, F.; Mathes, A.; Melchior, W.; M?ller, H.; Nuyken, O.; Spiegel, S., Angew. Makromol. Chem. (1992), 194,103. Byrn, S.R Solid-State Chemistry of Drug. (1983). Academic Press, New York. 162 Cesarin-Sobrinho, D. A influ?ncia de ?tomo de fl?or nos processos fotoqu?micos de Chalconas. Tese de Doutorado, Instituto de Ci?ncia Exatas, Universidade Federal do Rural do Rio de Janeiro, Serop?dica, (2001). Cesarin-Sobrinho, D.; Netto-Ferreira, J.; Quim. Nova. (2001). 5, 604-611. Cesarin-Sobrinho, D.; Netto-Ferreira, J.; Quim. Nova. (2002). 25, 62-68. Chan, W. C. W.; Nie, S. M. Science.(1998), 281 (5385), 2016?2018. Chang, H. C.; Popovitz-Biro, R.; Lahav, M.; Leiserowitz, L. J. Am. Chem. Soc. (1982), 104, 614?616. Chawla, H. M.; Chakrabarty, K., J. Chem. Soc. Perkin Trans. 1. (1984), 1511. Chawla, H. M.; Chiber, S. S.; Sharwa, A., Tetrahedron Lett. (1978), 19,2713. Chen, C.; Chang, V.; Cai, X.; Duesler, E.; Mariano, P. S. J. Am. Chem. Soc. (2001), 123, 6433 Chi, Y.M.; Nakamura, M.; Yoshizawa, T.; Zhao, X. Y.; Yan, W. M.; Hashimoto, F.; Kinjo, J.; Nohara, T.; Sakurada, S. Biol. Pharm. Bull. (2005), 28(9), 1776?1778. Chin, K. K.; Natarajan, A.; Gard, M. N.; Campos, L. M.; Shepherd, H.; Johansson, E.; Garcia-Garibay, M. A. Chem. Commun. (2007), 4266?4268. Choi, T.; Peterfy, K.; Khan, S. I.; Garcia-Garibay, M. J. Am. Chem. Soc. (1996), 118, 12477-12478. Chudgar, N. K.; Shah, S. N., Liquid Crystals. (1989), 4, 661. Chung, C.-M.; Roh, Y.-S.; Cho, S.-Y.; Kim, J.-G. Chem. Mater. (2004), 16, 3982?3984. Cia, X.; Chang, V.; Chen, C.; Kim, H.-J.; Mariaono, P. S. Tetrahedron Lett. (2000), 41, 9445. Ciamician, G.; Silber, P. Chem. Ber. (1908), 41, 1928. Ciamician, G.; Silber, P., Ber. Dtsch. Chein. Ges. (1901), 34, 2040. Cockburn, E.S.; Davidson, R.S.; Pratt, J.E. J. Photochem. Photobiol. A Chem. (1996), 94, 83?88. Cohen, M. D., Angew. Chem. Int. Ed. Engl. (1975), 14, 386 Cohen, M. D., Tetrahedron Lett. (1987), 43,1211. 163 Cohen, M. D.; Ludmer, Z. J. Chem. Soc., Chem. Commun. (1969), 1172-1173. Cohen, M. D.; Schmidt, G. M. J.; Sonntag, F. I., J. Chem. Soc. (1964), 2000. Colombier, I.; Spagnoli, S.; Corval, A.; Baldeck, P. L.; Giraud, M.; Leaustic, A.; Yu, P. Irie, M. J. Chem. Phys. (2007), 126, (011101/1-011101). Corey, E. J.; Mitra, R. B.; Uda, H. J. Am. Chem. Soc. (1964), 86, 485 Coxon, J. M.; Halton, B. Organic Photochemistry, Cambridge University Press, 1974. Craig, D. P.; Lindsay, R. N.; Mallett, C. P., Chem. Phys. (1984), 89, 187. Craig, D. P.; Mason, R.; Pauling, P.; Santry, D. P., Proc. Roy. Soc. A. (1965), 286, 98. Crimmins, M. T. Chem. Rev. (1988), 88, 1453. Crimmins, M. T.; Pace, J. M.; Nantermet, P. G.; Kim-Meade, A. S.; Thomas, J. B.; Watterson, S. H.; Wagman, A. S. J. Am. Chem. Soc. (2000), 122, 8453. Cunha, S.; Quim. Nova. (2008) 31( 4), 906-909. Cushing, B. L.; Kolesnichenko, V. L.; O?Connor, C. J. Chem.Rev. (2004), 104, 3893- 3946. Davaasambuu, J.; Busse, G.; S. Techert. J. Phys. Chem. A. (2006), 110, 3261-3265. De Mayo, P. de, Acc. Chem. Res. (1971), 4, 41. Debuigne, F.; Jeunieau, L.; Wiame, M.; Nagy, J. B. Langmuir. (2000), 16, 7605-7611. Dilling, W.L.; Tabor, T. E.; Boer, F.P.; North, P.P. J. Amer. Chem Soc. (1970), 92, 1399. Dolbier, W. R. Guide to fluorine NMR for organic chemists. John Wiley & Sons, Inc., Hoboken, New Jersey; (2009). Dunitz, J. Acta Crystallogr. (1995), B51, 619-631. Enoki, T. A. Caracteriza??o por espalhamento de luz de dispers?es aquosas de agregados lip?dicos ani?nicos. Disserta??o de mestrado. Instituto de F?sica, Universidade de S?o Paulo. (2010). Faria, A. P.; Visentin, L.C.; Bordinhao, J.; Cesarin-Sobrinho, D.; Netto-Ferreira, J.C. Acta Cryst. (2007), E63, 02770-02771. Feeder, N.; Honda, K. Mol. Cryst. Liq. Cryst. (1998), 313, 327?334. Fery-Forgues, Suzanne. Nanoscale. (2013), 5, 8428?8442. 164 Fischer, F.; Schuchardt, W.; Walter, H., Chem. Abst. (1970), 73, 7093y. Fouassier, J. P.; Merlin, A.; Journal of Photochemistry. (1980), 12(1), 17-23. Fu, H.-B.; Yao, J.-N. J. Am. Chem. Soc. (2001), 123, 1434-1439. Fu, X.; Xiong, Y.; Qingli, W.; Shuyun, X.; Shaona, Z.; Hu, Z. (2002), Colloids Surf. A Physicochem. Eng. Asp. (2002), 211(2-3), 249-258. Garcia-Garibay, M. A.; Constable, A. E.; Jernelius, J.; Choi, T.; Cizmeciyan, D.; Shin, S. H., L. Echegoyen and A. E. Kaifer (eds). in Physical Supramolecular Chemistry, (1996), 289. Giacomelli, F. C. Estrutura e Comportamento F?sico-Qu?mico de sistemas coloidais sob efeito de campo el?trico externo como perpspectiva para ci?ncia macromolecular. Tese de doutorado. Instituto de Qu?mica, Universidade Federal do Rio Grande do Sul. (2009). Gilchrist, T.L.; Storr, R. C.; Organic Reactions and Orbital Symmetry. Cambridge University Press, London, 192. Gnanaguru, K.; Ramasubbu, N.; Venkatesan, K.; Ramamurthy, V. A. J. Org. Chem. (1985), 50, 2337?2346. Gratzel, M. J. Photochem. Photobiol., A (2004), 164, 3-14. Gunder, O. A.; Vlasov, V. G.; Koval, L. N.; Krasovitski, B. M., Chem. Abst. (1968), 69, 36699y. Haleblian, J. K. Pharmaceut Sci.(1975). 64, 1269-1288. Hamer, G. K.; Peat, I. R.; Reynolds, W. F., Can. J. Chem. (1973), 51, 897 Han, R.O Organic Photochemistry, McGraw-Hill, New York, (1966). Hano, Y.; Itoh, N.; Hanoaka, A.; Yoshimitsu, I.; Nomura, T., Heterocycles, (1995), 41, 191. H?rtner, S.; Kim, H.-C.; Hampp, N. J. Polym. Sci. Part A: Polym. Chem. (2007), 45. Hasegawa, M. Adv. Phys. Org. Chern. (1995), 30, 117-171. Hasegawa, M.; Nahara, M.; Saigo, K.; Mori, T.; Nakanishi, H., Tetrahedron Lett. (1984), 25, 561-564. 165 Hasobe, T.; Imahori, H.; Fukuzumi, S.; Kamat, P. V. J. Phys. Chem. B. (2003), 107, 12105-12112. Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. (1991), 113, 8525. Heller, E.; Schmidt, G. M. J. Isr. J. Chem. (1971), 9,449-462. Hern?ndez-Linares, M. G.; Guerrero-Luna, Gabriel.; Perez-Estrada, S.; Ellison, M.; Ort?n, M.M.; Garcia-Garibay, M. A. J. Am. Chem. Soc. (2015), 137 (4), 1679?1684. Hirata, Y.; Mataga, N. Chem. Phys. Lett. (1992), 193, 287. Hirata, Y.; Okada, T.; Mataga, N.; Nomoto, T. J. Phys. Chem. (1992), 96, 6559. Honda, K.; Nakanishi, F.; Feeder, N. J. Am. Chem. Soc. (1999), 121, 8246?8250. Ichimura, K. J. Polym.Sci. Part A. (1982), 20, 1411?1417. Ichimura, K.; Oohara, N. J. Polym. Sci. Part A. (1987), 25, 3063?3077. Ichimura, K.; Watanabe, S. J. Polym. Sci. Part A. (1982), 20, 1419?1432. Ihmels.; H. Scheffer, J. R. Tetrahedron. (1999), 55, 885-907. Innes, K. K., J. Mol. Spectrosc. (1983), 97, 420. Israelachivili, J. N. Intermolecular and Surfaces Forces. (1985). Academic Press, Orlando. Iwata, S.; Nishino, T.; Nagata, N.; Satomi, Y.; Nishino, H.; Shibata, S., Biol. Pharm. Bull., (1995), 18, 1710. Jarvis, A. G., Sparkes, H. A., Tallentire, S. E., Hatcher, L. E., Warren, M. R., Raithby, P. R., Allan, D. R., Whitwood, A. C., Cockett, M. C. R., Duckett, S. B., Clark, J. L., Fairlamb, I. J. S.; CrystEngComm. (2012), 14, 5564?5571. Javadian, S.; Ruhi, V.; Heydari, A.; Shahir A. A.; Yousefi, A.; Akbari. J. Ind. Eng. Chem. Res. (2013), 52, 4517-4526. Jing, L. H. Acta Cryst. (2009). E65, o2515. Jones, W.; Nakanishi, H.; Thomas, J. M., J. Chem. Soc., Chem. Commun. (1980), 610. Jong, A. W. K. de ., Ber. Dtsch. Chem. Ges. (1923), 56, 818. Kamal, A.; Dastagiri, D.; Ramajah, M. J.; Reddy, J. S.; Bharathi, E. V.; Srinivas, C.; Pushpavalli, S. N. C. V. L.; Pal, D.; Pal-Bhadra, M.; Chemmedchem. (2010). 5, 1947. 166 Karaki-Doy, T.; Nakagawa, T.; Kasai, T. Y.; Goto, Y., J. Electrochem. Soc. (1995), 142, 4257. Kasai, H.; Kamatani, H.; Okada, S.; Oidawa, H.; Matsuda, H.; Nakanishi, H. Jpn. J. Appl. Phys. (1996), 35, L221-L223. Kasai, H.; Nalwa, H. S.; Oikawa, H.; Okada, S.; Matsuda, H.; Minami, N.; Kakuta, A.; Ono, K.; Mukoh, A.; Nakanishi, H. Jpn. J.Appl. Phys. (1992), 31, L1132-L1134. Katzenellenbogen, E. R.; Branch, G. E. K., J. Am. Chem. Soc. (1947), 69, 1615. Kaupp, G.: Solid-state reactions. Curr. Opin. Solid State Mat. Sci. (2002), 6, 131?138. Kawaki, T.; Kobayashi, M.; Hayashi, K.; Watanabe, M.; Honda, W., Chem. Abst. (1989), 110, 58274y. Keating, A. E.; Garcia-Garibay, M. A.; Ramamurthy, V.; Schanze, K. S. Photochemical solid-to-solid reactions. In Organic and Inorganic Photochemistry. ed. Marcel Dekker: New York, (1998). Keuren, E. V.; Georgieva, E.; Adrian, J. Nanoletters. (2001), 1, 141-144. Kim, H. Y.; Bjorklund, T. G.; Lim, S.-H.; Bardeen, C. J. Langmuir. (2003), 19, 3941- 3946. Kim, H.-C., H?rtner, S., Behe, M., Behr, T.M., Hampp, N., J. Biomed. Opt. 11. (2006), 34024. Kim, N.; Leeb, G. S.; Cuia, C.; Ahna, D.J., Synthetic Metals. (2016), 213, 42-46. Kim, T.; Zhu, L.; Mueller, L. J.; Bardeen, C. J. CrystEngComm. (2012), 14, 7792? 7799. Klimov, V. I.; Mikhailovsky, A. A.; Xu, S.; Malko, A.; Hollingsworth, J. A.; Leatherd C. A.; Eisler, H.-J.; Bawendi, M. G. Science. (2000), 290, 314-317. Kobatake, S.; Takami, S.; Muto, H.; Ishikawa, T.; Irie, M. Nature. (2007), 446, 778? 781. Kohler, E. P.; Chadwell, H. M., in Org. Synth. Coll.; John Wiley: New York, (1932), 1, 78. Koivukorpi, J.; Kolehmainen, E. Journal of Molecular Structure. (2009), 930, 116? 120. Kopeck, J. ; Organic Photochemistry; VCH Publishers,Inc (1992). 167 Koshima, H.; Ojima, N.; Uchimoto, H. J. Am. Chem. Soc. (2009), 131, 6890?6891. Kumar, V.A., Begum, N.S., K. Venkatesan, J. Chem. Soc. Perkin Trans. 2. (1993) 463? 467. Kuzmanich, G.; Natarajan, A.; Chin, K. K.; Veerman, M.; Mortko, C. J.; Garcia- Garibay, M. A. J. am. chem. soc. (2008), 130, 1140-114. Kuzmanich, G.; Simoncelli, S.; Gard, M. N.; Spanig, F.; Henderson, B. L.; Guldi, D. M.; Garcia-Garibay, M. A. J. Am. Chem. Soc. (2011), 133, 17296?17306. Kuzmanich, G.; Vogelsberg, C. S.; Maverick, E. F.; Netto-Ferreira, J. C, Scaiano, J. C.; Garcia-Garibay, M. A. J. Am. Chem.Soc. (2012), 134, 1115?1123. Kuzmanich, G.; Xue, J.; Netto-Ferreira, J. C.; Scaiano, J. C..;b Platz, M.; Garcia- Garibay, M. A. Chem. Sci. (2011), 2, 1497. Kwon, E.; Oikawa, H.; Kasai, H.; Nakanishi, H., Crystal Growth & Design. (2007), 7(4), 600-602. LaMer, V. K.; Dinegar, R. H. J. Am. Chem. Soc. (1950), 72, 4847-4854. Lange, C. W.; Foldeaki, M.; Nevodchikov, V. I.; Cherkasov, V. K.; Abakumov, G. A.; Pierpont, C. G. J. Am. Chem. Soc. (1992), 114, 4220?4222. Lawrence, N. J.; Patterson, R,P., Ooi, L,L., Cook, D., Ducki, S., Biooganic & Medicinal Chemistry Letters. (2006), 16, 5848. Lee, G. S.; Kim, E. S.; Cho, S. I.; Kim, J. H.; Choi, G.; Ju, Y. S.; Park, S. H.; Jeong, S. I.; Kim, H. I.; J. Of Soc. Korean. Biol. Chem. (2010). 53, 290. Lee, X. Z. ; Liang, Y. R.; Chen, H.; Lu, J. L.; Liang, H. L. ; Huang, F. P.; Mamati, E.; J. Afric. Biotechnol. (2008). 7, 4115. Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. (1997), 119 1462?1463. Leiserowitz, L.; Schmidt , G. M. J., J. Chem. Soc. A, (1969), 2372. Leska, J.; Zaharadnik, P., Chechoslov. Chem. Commun., (1973), 3365. Li, R.; Kenyon, G. L.; Cohen, F. E.; Chem, X.; Gong, B.; Miller, R. E.; Nuzum, E. O.; Resenthal, P. J.; McKerrow, J. H., J. Med. Chem. (1995), 38, 5031. 168 Libermann, C., Chem. Ber. (1889), 22, 124. Libermann, C., Chem. Ber. (1889), 22, 782. Liu, J.; Boarman, K.J. Chem. Commun. (2005) 340?341. Liu, X.; Deng, R.; Zhang, Y.; Wang, Y.; Chang, H.; Huang, L.; Liu, X. Chem. Soc. Rev. (2015), 44 (6), 1479?1508. Lo, P. C.-K.; Snapper, M. L.; Org. Lett. 2001, 3, 2819. Lutz, E. R.; Jordan, R. H.; Chemical Laboratory of the university of Virginia. (1950), 4090. Mahe, L.; Izouoka, A.; Sugawara, T. J. Am. Chem. Soc. (1992), 114,7904-7906. Matos, M. J.; Vazquez-Rodriguez, S.; Uriarte, E.; Santana, L. Expert Opin. Ther. Patents. (2014), 25(3). Matsui, A. H.; Mizuno, K.; Nishi, O.; Matsushima, Y.; Shimizu, M.; Goto, T.; Takeshima, M. Chem. Phys. (1995), 194, 167-174. Matsushima, R.; Hirao, I., Bull. Chem. Soc. Jpn. (1980), 53, 518. Mc Crone, W.C Polymorphism. (1975). Jonh Wiley & Sons, 2, 725-762. McDonald, T. O.; Martin, P.; Patterson, J. P.; Smith, D.; Giardello, M.; Marcello, M.; See, V.; O?Reilly, R. K.; Owen, A.; Rannard, S. Adv Funct. Mater. (2012), 22, 2469- 2478. Minsk, L.M.; Smith, J.G.; Van Deusen, W.P.; Wright, J.F. J. Appl. Polym. Sci. (1959), 2, 302?307. Miquel, J. F., Comp. Rend., (1964), 254, 4479. Montaudo, G.; Librando, V.; Caccamese, S.; Maravign, P., J. Am. Chem. Soc., 1973, 95, 6365. Moorthy, J. N.; Mal, P.; Tetrahedron Letters. (2003), 44(12), 2493-2496. Morimoto, M.; M. Irie. J. Am. Chem. Soc., (2010), 132, 14172?14178. Mortko, C J.; Dang, H.; Campos, L. M.; arc a-Garibay, M. A. Tetrahedron Letters. (2003), 44, (32), 6133-6136. Mortko, C. J.; Garcia-Garibay. J. Am. Chem. Soc. (2005), 127, 7994-7995. 169 Muraoka, O.; Okumura, K.; Maeda, T.; Tanabe, G.; Momose, T. Tetrahedron: Asymmetry. (1994), 317-320. Murthy, G. S.; Arjuna, P.; Venkatesan, K.; Ramamurthy, V. Tetrahedron. (1987), 43, 1225-1240. Nakanishi, H.; Jones, W.; Thomas, J. M. Chem. Phys. Lett. (1980), 71, 44?48. Nakanishi, H.; Nakano, N.; Hasegawa, M. J. Polym. Sci., B: Polym. Lett. (1970), 8, 755. Naumov, P.; Kowalik, J.; Solntsev, K. M.; Baldridge, A.; Moon, J.S.; Kranz, C.; Tolbert, L. M. J. Am. Chem. Soc. (2010), 132, 5845?5857. Netto-Ferreira, J. C.; Wintgens ,V.; Scaiano, J. C. Can. J. Chem. (1994), 72, 1565. Netto-Ferreira, J. C.; Wintgens, V.; Scaiano, J. C.; J. Braz. Chem. Soc. (1997), 8, 427. Netto-Ferreira, J. C.; Wintgens, V.; Scaiano, J. C. Tetrahedron Lett. (1989), 30, 6851? 6854. Neugebauer, J. M. Meth. Enzymol. (1990), 182, 239-253. Ng, D.; Yang, Z.; Garcia-Garibay, M. A. Tetrahedron Letters. (2001), 42, 9113?9116. Ng, D.; Yang, Z.; Garcia-Garibay, M. A. Tetrahedron Letters. (2002), 43, 7063?7066. Nowakowska, Z. European Journal of Medicinal Chemistry. (2007), 42, 125-137. Ohashi, Y., Acc. Chem. Res. (1988), 21, 268. Ohkura, K.; Kashino, S.; Haisa. Bulletin of the Chemical Society of Japan. (1973), 46, 627-628. Oikawa H, Kasai H, Nakanishi H. Fabrication of organic microcrystals and their optical properties (Cap?tulo 11); Some applications of organic microcrystals (Cap?tulo 12). In: Glaser R, Kaszynski P (eds) Anisotropic organic materials ?approaches to polar order. ACS symposium series 798. ACS, Washington (2001), 169. Oikawa H, Masuhara A, Kasai H, Mitsui T, Sekiguchi T, Nakanishi H. Organic and polymer nanocrystals: their optical properties and function (Cap?tulo 13). In: Masuhara H, Kawata S (eds) Handai nanophotonics ?nanophotonics: integrating photochemistry, optics and nano/bio materials studies. Elsevier, Amsterdam, (2004). 170 Oikawa H, Nakanishi H. Reprecipitation method for organic nanocrystals (Cap?tulo 2); Optical properties of polymer nanocrystals (Cap?tulo 14); Particle-based optical devices (Cap?tulo 29). In: Masuhara H, Nakanishi H, Sasaki K (eds) Nano science and technology ?single organic nanoparticles. Springer, Berlin, (2003), 169, 382 Oikawa, H.; Mitsui, T.; Onodera, T.; Kasai, H.; Nakanishi, H.; Sekiguchi, T.; Jpn. J. Appl. Phys. (2003) 42, L111. Okuma, O.; Takenochi, M.; Miyagawa, M., Chem. Abst. (1989), 110, 66933c. Oumi, M.; Maurice, D.; Head-Gordon, M. Spectrochimica Acta Part A. (1999) 55, 525? 537. Paul, T.; Hassan, M. A.; Korth, H.-G.; Sustmann, R.; Avila, D. V. J. Org. Chem. (1996), 61, 6835. Paula, A. F. Estudo da fotodimeriza??o de chalconas fluoradas no estado s?lido cristalino. Disserta??o de Mestrado, Instituto de Ci?ncia Exatas, Universidade Federal do Rural do Rio de Janeiro, Serop?dica, (2007). Poloukhtine, A.; Popik, V. V. J. Phys. Chem. A. (2006), 110, 1749. Prinzabach, Pure and Applied Chem, (1968), 16,17. Rabinovich, D. J. Chem Soc. (B), (1970). Ramamurthy, V.; Sivaguru, J. Chem Rev. (2016), xxx, xxxx-xxxx. Ramamurthy, V.; Venkatesan, K. Chem Rev. (1987), 87, 433-481. Randall, M. L.; Lo, P. C.-K.; Bonitatebus, P. J.; Snapper, M. L., J. Am. Chem. Soc. (1999), 121, 4534. Regos, I.; Treutter, D.; J. of. Chromat. (2010), 1217, 6169. Reiser, A.; Egerton, P.L. Photogr. Sci. Eng. (1979), 23, 144?150. Rezaie, R.; Mohammad, H.; Navid, M. S. R. J. Chin. Chem. (2011), 29, 1226. Rojas, J.; Paya, M.; Devesa, I.;. Archives of Pharmacol. (2003), 368, 233. Rojas, J.; Paya, M.; Dominguez, J. N.; Bioogarnic & Med. Chem. (2002), 12, 1954. Rozmer, Z.; Perj?si, P. Phytochem Rev. (2016), 15(1), 87-120. 171 Sakamoto, M. Chem. Eur. J. (1997), 3,684-689. Sashida, Y.; Ogawa, K. M.; Kitada, M.; Karikone, H.; Mimaki, Y.; Shimomura, H., Chem. Pharm. Bull. (1991), 39, 709. Scaiano, J. C.; Wintgens, V.; Netto-Ferreira, J. C. Pure Appl. Chem. (1990), 62, 1557? 1564. Schaller, R. D.; Klimov, V. I. Phys. Rev. Lett. (2004), 92, 186601/1-4. Scheffer, J. R.; Garcia-Garibay, M.; Nalamasu, O. Org. Photochem. (1989), 8, 249-347. Schellenberg, W. D.; Jakoby, H., Chem. Abst., 1961, 55, 7119e. Schmidt, G. M. J., J. Chem. Soc. (1964), 2014. Schuetz, S. A.; Bowman, E. A.; Sivernail, C. M.; J. of. Orga. Chem. (2005). 690, 1017. Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. (1993), 93, 3. Schwarzer, A.; Weber E. Acta Cryst. (2010). E66, o1931. Sean, W. R.; Hao, C.; Hanxiao, J.; J. Mol. Cataly. (2010), 66, 263. Senier, A.; Shephard, F. G. J. Chem. Soc. (1909), 95, 1943. Shih, C.H; Chu, H; Tang, L. K; Sakamoto, W.; Maekewa, M.; Chu, I. K.; Wang, M.; Lo, C.; J of botany. (2008). 228, 1054. Shin, H. S.; Keating, A. E.; Garcia-Garibay, M. A. J. Am. Chem. Soc. (1996), 118, 7626-7627. Shin, S.; Cizmeciyan, D.; Keating, A. E.; Khan, S.; Garcia-Garibay, M. A. J. Am.Chern. Soc. (1997), 119, 1859-1868. Sinnwell, M. A., Ingenthron, B. J., Groeneman, R. H., MacGillivray, L.R. Journal of Fluorine Chemistry. (2016). 188, 5?9. Skloss, T.W.; Haw, J.F. Macromolecules. (1994), 27, 6998?6999. Sol?niov?, E.; Toma, S.; Gronowitz, S., Org. Mag. Res. (1976), 8, 439. Sonoda, Y.; Goto, M.; Tsuzuki, S.; Akiyama, H.; Tamaoki, N.; Journal of Fluorine Chemistry. (2009), 130, 151-157. Stevens, B.; Dickinson, T.; Sharpe, R. R. Nature. (1964), 204, 876-877. Stobbe, H.; Steinberger F. K. Ber. Dtsch. Chem. Ges. (1922), 55, 2225. 172 Swiatkiewicz, J.; Eisenhardt, G.; Prasad, P. N.; Thomas, J. M.; Jones,W.; Theocharis, C. R. J. Phys. Chem. (1982), 86, 1764?1767. Szmant, H. H.; Basso, A. J., J. Am. Chem. Soc. (1952), 74, 4397. Takahashi, S.; Miura, H.; Kasai, H.; Okada, S.; Oikawa, H.; Nakanishi, H. J. Am. Chem. Soc. (2002), 124, 10944?10945. Takeuchi, S.; Tahara, T. J. Chem. Phys. (2004), 120, 4768. Tanaka, R.; Suzuki, I.; Yamaguchi, A.; Misawa, H.; Sakuragi, H.; Tokumaru, K. Tetrahedron Letters. (1992), 33, (25), 3651-3654. Terazima, M.; Hara, T.; Hirota, N. Chem. Phys. Lett. (1995), 246, 577. Tom?s, A. J. C. Polimeriza??o de cloreto de vinilo em fase dispersa: desenvolvimento e caracteriza??o de novos produtos e optmiza??o do processo. Disserta??o apresentada ? Faculdade de Ci?ncias e Tecnologia da Universidade de Coimbra, para a obten??o do grau de Doutor em Engenharia Qu?mica, na especialidade de Sistemas e Processos Qu?micos, Coimbra. (2009). Tr?ger, J., H?rtner, S., Heinzer, J., Kim, H.-C., Hampp, N. Chemical Physics Letters (2008), 455, 307?310. Tran, H.D.; Li, D.; Kaner, R.B., Adv. Mater. (2009), 21, 1487?1499. Tsukerma, S. V.; Surov, Y. N.; Lavrushi, V. F., Zh. Obshch. (1967), 38, 524. Turowska-Tyrk, I. Chem. Eur. J. (2001), 7, 3401?3405. Turowska-Tyrk,I.; Trzop, E. Acta Crystall. Section B. (2003), 59, 779-786. Turro, N. J. Modern Molecular Photochemistry. The Benajmin/Cummings Publishing Company Inc.: Menlo Park; (1978). Turro, N. J. Modern Molecular Photochemistry. The Benajmin/Cummings Publishing Company Inc.: Menlo Park; (1978). Uchida, K.; Sukata, S.; Matsuzawa, Y.; Akazawa, M.; Jong, J. J. D. d.; Katsonis, N.; Kojima, Y.; Nakamura, S.; Areephong, J.; Meetsma, A.; Feringa, B. L. Chem.Commun. (2008), 326?328. Ujiiye-Ishii, K.; Kwon, E.; Kasai, H.; Nakanishi, H.; Oikawa, H. Crystal Growth & Design. (2008), 8 (2), 369-371. 173 Veerman, M.; Resendiz M.J. E.; Garcia-Garibay, M. A. Organic Letters. (2006), 8(12), 2615-2617. Venkateschwarlu, G.; Subrahmanyam, B., Proc. Indian Acad. Sci. (Chem. Sci). (1990), 102, 45. Vishnumurthy, K.; Row, G.; T.N., K. Venkatesan, Tetrahedron 55. (1999), 4095?4108. Vishnumurthy, K.; Row, T.N.G., K. Venkatesan, J. Chem. Soc. Perkin Trans. 2. (1996), 1475?1478. Vishnumurthy, K.; Guru Row, T.N.; Venkatesan, K. J. Chem. Soc. Perkin Trans. 2 (1996), 1475?1478. W. Marckwald, Z. Phys. Chern. (1899), 30, 140. Walczak, B.; Dreux, M.; Chretien, J. R., Chomatographia. (1991), 31, 575. Wang, Y. Li.; Xia, R.; Scien. Hortic. (2010), 125, 116. Warpeha, K. M.; Gibbons, J., Carol, A.; Slusser, J.; Tree, R.; Durham, W.; Kaufman, L S.; Plant. And. Enviroment. (2008). 31, 1770. Wegner, G., Pure Appl. Chem. (1977), 49, 443. Weygand, C., Ann. Chem. (1929), 472, 154. White, J. D.; Kim, J.; Drapela, N. E. J. Am. Chem. Soc. (2000), 122, 8665. Williams, D. E., J. Chem. Phys. (1966), 45, 3770. Winkler, J. D.; Axten, J. M. J. Am. Chem. Soc. (1998), 120, 6425. Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. (1995), 95, 2003. Wu, M. H..; Yang, X.H.; Zou,W. D.; Liu, W.J.; Li, C. Z. Kristallogr. NCS, (2006), 221 323-324. Yagita, Y.; Matsui, K. Journal of Luminescence. (2015), 161, 437?441. Yamauchi, S.; Hirota, N.; Higuchi, J., J. Phys. Chem. (1988), 92, 2129. 174 Yang, K.; He, J. A.; Kumar, J.; Samuelson, L. A; Oshikiri, T.; Katagi, H.; Kasai, H.; Okada, S.; Oikawa, H.; Nakanoshi, H.; Tripathy, S. K. J. Opt. Soc. Am. B. (2005), 22(3), 623-632. Yang, Z.; Ng, D.; Garcia-Garibay, M. A. J. Org. Chem. (2001), 66, 4468-4475. Yayli, N.; U?uncu, O.; Aydin, E.; Gok, Y.; Yasar, A.; Baltaci, C.; Yildirim, N.; KucuK, M. Journal of Photochemistry and Photobiology A: Chemistry. (2005) 169, 229?234. Zhang, J.; S, Li.; An, F. F.; Liu, J.; Jin, S.; Zhang, J. C.; Wang, P. C.; Zhang, X.; Lee, C. S.; Liang, X. J. Nanoscale. (2015), 7, 13503?13510. Zhang, X. F.; Zhang, Y. K. Dyes and Pigments. (2015), 120, 265-270. http://disciplinas.stoa.usp.br/pluginfile.php/374074/mod_resource/content/1/DLS.pdf visitada em 23/07/2016 ?s 13hs. http://www.intechopen.com/ books/nanocrystal/functional-organic- nanocrystals, visitada em 30/08/16 ?s 18 hs. https://social.stoa.usp.br/articles/0016/2139/Aula_Thais.pdf, visitada em 23/07/2016 ?s 13:30 hs. |
Page generated in 0.0068 seconds