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Titolo:
PHOTOPHYSICS AND PHOTOCHEMISTRY OF INTRAMOLECULAR STILBENE-AMINE EXCIPLEXES
Autore:
LEWIS FD; BASSANI DM; BURCH EL; COHEN BE; ENGLEMAN JA; REDDY GD; SCHNEIDER S; JAEGER W; GEDECK P; GAHR M;
Indirizzi:
NORTHWESTERN UNIV,DEPT CHEM,2145 SHERIDAN RD EVANSTON IL 60208 UNIV ERLANGEN NURNBERG,INST PHYS & THEORET CHEM W-8520 ERLANGEN GERMANY
Titolo Testata:
Journal of the American Chemical Society
fascicolo: 2, volume: 117, anno: 1995,
pagine: 660 - 669
SICI:
0002-7863(1995)117:2<660:PAPOIS>2.0.ZU;2-H
Fonte:
ISI
Lingua:
ENG
Soggetto:
AMINOALKYL RADICAL FORMATION; FLUORESCENCE QUANTUM YIELDS; ELECTRON-TRANSFER; STYRENE-AMINE; ADDITION-REACTIONS; ALIPHATIC-AMINES; TERTIARY-AMINES; CIS-STILBENE; DERIVATIVES; TEMPERATURE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
69
Recensione:
Indirizzi per estratti:
Citazione:
F.D. Lewis et al., "PHOTOPHYSICS AND PHOTOCHEMISTRY OF INTRAMOLECULAR STILBENE-AMINE EXCIPLEXES", Journal of the American Chemical Society, 117(2), 1995, pp. 660-669

Abstract

The photophysical and photochemical behavior of a series of trans-(aminoalkyl)stilbenes in which a primary, secondary, or tertiary amine isappended to the stilbene ortho position with a methyl, ethyl, or propyl linker has been investigated. The tertiary (aminoalkyl)stilbenes form fluorescent exciplexes and undergo trans-cis isomerization, but fail to undergo intramolecular reactions analogous to intermolecular addition reactions observed for stilbene with tertiary amines. The photophysical behavior of the tertiary (aminoalkyl)stilbenes is dependent upon the choice of linker, solvent, and temperature. The secondary (aminoalkyl)stilbenes do not form fluorescent exciplexes but undergo intramolecular N-H addition to the stilbene double bond. Unlike the intermolecular reactions of substituted stilbenes with secondary amines, which yield mixtures of regioisomeric adducts and reduction products, the intramolecular reactions are highly selective, providing an efficient method for the synthesis of tetrahydrobenzazepines. Direct irradiation of the primary (aminoalkyl)stilbenes results only in trans-cis isomerization. However, irradiation in the presence of the electron acceptor p-dicyanobenzene results in regioselective intramolecular N-H addition to the stilbene double bond. These results are discussed in terms of the mechanisms of direct and electron-transfer-sensitized irradiation.

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Documento generato il 29/11/20 alle ore 06:50:56