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Anomalous photophysics of bis(hydroxystyryl)benzenes: a twist on the para/meta dichotomy.

  作者 Solntsev, Kyril M.;McGrier, Psaras L.;Fahrni, Christoph J.;Tolbert, Laren M.;Bunz, Uwe H. F.;  
  选自 期刊  Organic Letters;  卷期  2008年10-12;  页码  2429-2432  
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[摘要]Photographic and Other Reprographic Processes) Section The two isomeric bis(hydroxystyryl)benzenes HO-p-C6H4-CH=CH-C6H4-p-OH (I) and HO-m-C6H4-CH=CH-C6H4-m-OH (II) show dramatically different photophys. properties that are distinct from each other and from smaller 3- and 4-hydroxystilbenes. A dianion of I is highly fluorescent when dianion of II is completely nonfluorescent. The large quantum yield of fluorescence of I and its dianion reflects a planarized and quite rigid excited-state with quinoidal resonance contribution, while the quenching of the dianion of II maybe explained by the presence of an intermediate 3(n-p*) state combined with poor Franck-Condon overlap between the HOMO and LUMO of this double phenolate.

 
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