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PHOTO RETRO DIELS-ALDER REACTION OF THE ADDUCTS OF TETRACYANOETHYLENE AND POLYAROMATIC COMPOUNDS

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Date Issued:
2011
Abstract/Description:
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 > TCNE/anthracene > 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.
Title: PHOTO RETRO DIELS-ALDER REACTION OF THE ADDUCTS OF TETRACYANOETHYLENE AND POLYAROMATIC COMPOUNDS.
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Name(s): Banerjee, Siddthartha, Author
Liao, Yi, Committee Chair
University of Central Florida, Degree Grantor
Type of Resource: text
Date Issued: 2011
Publisher: University of Central Florida
Language(s): English
Abstract/Description: 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 > TCNE/anthracene > 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.
Identifier: CFE0004029 (IID), ucf:49165 (fedora)
Note(s): 2011-08-01
M.S.
Sciences, Department of Chemistry
Masters
This record was generated from author submitted information.
Subject(s): Phto-retro Diels-Adler reaction
retro-diels alder reaction
photo reactive Diels-Alder adduct
Persistent Link to This Record: http://purl.flvc.org/ucf/fd/CFE0004029
Restrictions on Access: public
Host Institution: UCF

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