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Title Regioselective trans-cis photoisomerization of m-styrylstilbenes
Creator/Author Ito, Y. ; Uozy, Y. ; Dote, T. ; Ueda, M. ; Matsuura, T.
Publication Date1988 Jan 06
OSTI IdentifierOSTI ID: 7004335
Other Number(s)CODEN: JACSA
Resource TypeJournal Article
Resource RelationJ. Am. Chem. Soc. ; Vol/Issue: 110:1
Research OrgKyoto Univ. (Japan)
Subject400500 -- Photochemistry; STILBENE-- ISOMERIZATION;STILBENE-- PHOTOCHEMICAL REACTIONS; ABSORPTION SPECTROSCOPY;EXCITED STATES;EXPERIMENTAL DATA;NMR SPECTRA;NUCLEAR MAGNETIC RESONANCE;PHOTOCHEMISTRY;QUANTUM EFFICIENCY;RADIATIONLESS DECAY;TRIPLETS
Related SubjectAROMATICS;CHEMICAL REACTIONS;CHEMISTRY;DATA;DE-EXCITATION;EFFICIENCY;ENERGY LEVELS;ENERGY TRANSFER;ENERGY-LEVEL TRANSITIONS;HYDROCARBONS;INFORMATION;MAGNETIC RESONANCE;MULTIPLETS;NUMERICAL DATA;ORGANIC COMPOUNDS;RESONANCE;SPECTRA;SPECTROSCOPY
Description/Abstract Trans-cis photoisomerization of m-styrylstilbenes, i.e., 2,4,6-triisopropyl-3`-styrylstilbene (TISS), 2,4,6-trimethyl-3`-styrylstilbene (TMSS), and 3-styrylstilbene (SS), and of stilbenes, i.e., 2,4,6-triisopropylstilbene (TIS), 2,4,6-trimethylstilbene (TMS), and stilbene (S), are studied under direct of benzophenone-sensitized irradiation in hexane.^Measurements of quantum yields of isomerization have revealed that although the styrylstilbene molecule bears two styryl groups, the reaction is highly regioselective, depending upon the excitation conditions and reactant structures.^For example, isomerization of trans, trans-TISS and trans,cis-TISS occurred either at the 2,4,6-trisubstituted styryl side upon direct excitation or at the unstubstituted styryl side upon sensitized excitation.^When the starting material carries an unsubstituted cis-styryl group, the major isomerization always occurred at this moiety by either direct or sensitized excitation, e.g., cis,trans-TISS ..-->.. trans,trans-TISS, cis,cis-TISS ..-->.. trans,cis-TISS, and cis,trans-SS ..-->.. trans,trans-SS.^Furthermore, the photoisomerization of cis,cis-SS was found to be one-way.^These results are interpreted in terms of the usual energy sink concept: the excited-state energies (E/sub S/ and E/sub T/) of the stilbene chromophores depend on molecular distortion in a subtle manner.
Country of PublicationUnited States
LanguageEnglish
FormatPages: 189-198
System Entry Date2001 May 13

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