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Complexation of camphor sulfonic acid to affect the emission behavior of organic compound and polymer with quinoline moiety

Many chromophoric organics and polymers are highly emissive in their dilute
solutions but become weakly luminescent in the high concentration and solid film states
due to the induced £k−£k interactions of the intimately-contact chromophores. Therefore, it
is practically important to develop fluorescent organic and polymeric materials with
enhanced emission in their aggregated states (so called aggregated-induced emission,
AIE). In this study, organic compound 2,4-diphenylquinoline (DPQ) with inherent
quinoline ring and polymeric poly(vinyl diphenylquinoline) (PVQ) with pendant
quinoline group were prepared and their AIE-phenomena were characterized. To prove the
reported point that restriction of intramolecular rotation (RIR) is the main cause for AIE
effect, DPQ and PVQ were further incorporated with organic strong acid of
camphorsulfonic acid (CSA). Through the favorable acid-base interaction between the
sulfonic acid in CSA and the nitrogen atom of the quinoline ring in DPA (or CSA), ionic
complex of DPQ-CSA (and PVQ-CSA) was easily prepared and their response toward
AIE properties were studied. Through the enhanced RIR by the complexation of bulky
CSA with the central quinoline ring, the resulting DPQ-CSA (and PVQ-CSA) complex
was proved to have better AIE-effect compared to the pristine DPQ (and PVQ). RIR
mechanism can be indirectly proved in this case.
We study the AIE on micelle topics of the block copolymer. We choose the
poly(styrene-block-tertbutylstyrene) (PS-b-PBS) as our block copolymer. To synthesize
the PS-b-PBS, we can successfully get the new block copolymer PVQ-b-PBS.
PVQ-b-PBS was similarly blended with the CSA. In the block copolymer micelles, choose
the selective solvent to get the different micelles and observe the diverse on the
luminescence. Finally, we analyzed compositions and conformations by atomic force
microscopy (AFM) and transmission electron microscopy (TEM).

Identiferoai:union.ndltd.org:NSYSU/oai:NSYSU:etd-0728110-101145
Date28 July 2010
CreatorsChou, Chein-an
ContributorsJ.L. Hong, S.W. Kuo, Y.W. Chiang, M. Chen
PublisherNSYSU
Source SetsNSYSU Electronic Thesis and Dissertation Archive
LanguageEnglish
Detected LanguageEnglish
Typetext
Formatapplication/pdf
Sourcehttp://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0728110-101145
Rightsrestricted, Copyright information available at source archive

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