Thermally induced retro-Diels Alder (rDA) reaction has been extensively used for the preparation of many reactive intermediates in organic synthesis. But the uses of photo-retro Diels-Alder (PrDA) reaction in organic synthesis were sparingly reported in literature. Due to its spatial and temporal control, PrDA can be used in making of photosensitive materials, in drug delivery and also for mechanistic studies. Diels-Alder adducts of tetracyanoethylene (TCNE) and polyaromatic compounds (anthracene, napthacene, pentacene and phencyclone) were synthesized and were subjected to PrDA reaction through 254-nm irradiation. The quantum yield and the consequent photoreactivity of these DA adducts follow the following order. TCNE/naphthacene greater than] TCNE/anthracene greater than or equal to] TCNE/pentacene This trend was explained by a mechanism of charge-separated intermediates. The stability of the charge-separated intermediate is the governing factor of this trend of photoractivity of DA adducts. Based on these results it is possible to design a proper DA adduct and consequently predict the feasibility of the PrDA reaction.
| Identifer | oai:union.ndltd.org:ucf.edu/oai:stars.library.ucf.edu:etd-2898 |
| Date | 01 January 2011 |
| Creators | Banerjee, Siddthartha |
| Publisher | STARS |
| Source Sets | University of Central Florida |
| Language | English |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | Electronic Theses and Dissertations |
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