Benzo[a]imidazo[5,1,2-cd]indolizines - a new class of molecules displaying excited state intramolecular proton transfer (Articolo in rivista)

Type
Label
  • Benzo[a]imidazo[5,1,2-cd]indolizines - a new class of molecules displaying excited state intramolecular proton transfer (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1039/c3nj00842h (literal)
Alternative label
  • Stasyuk, Anton J.; Banasiewicz, Marzena; Ventura, Barbara; Cyranski, Michal K.; Gryko, Daniel T. (2014)
    Benzo[a]imidazo[5,1,2-cd]indolizines - a new class of molecules displaying excited state intramolecular proton transfer
    in New journal of chemistry (1987)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Stasyuk, Anton J.; Banasiewicz, Marzena; Ventura, Barbara; Cyranski, Michal K.; Gryko, Daniel T. (literal)
Pagina inizio
  • 189 (literal)
Pagina fine
  • 197 (literal)
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  • 38 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 9 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 1 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Warsaw University of Technology; University of Warsaw; Polish Academy of Science; Consiglio Nazionale delle Ricerche (CNR) (literal)
Titolo
  • Benzo[a]imidazo[5,1,2-cd]indolizines - a new class of molecules displaying excited state intramolecular proton transfer (literal)
Abstract
  • The new class of ESIPT-capable molecules, benzo[a]imidazo[5,1,2-cd]indolizines, bearing the 2-hydroxyPhenyl substituent were prepared in a straightforward manner from imidazo(1,2-alpyridines via a tandem [8+2]cycloaddition-[2+6+2]dehydrogenation reaction. The relationship between the structure and photophysical properties was thoroughly elucidated by comparison with simple analogues i.e. 2-(2'-hydroxyphenyl)imidazo[1,2-alpyridines. Compared with parent 2-(2'-hydroxyphenyl)imidazo[1,2-a]pyridines the new chromophores strongly absorb blue light and emit in the yellow part of the spectrum. In contrast to 2-(2'-hydroxyphenypimidazo[1,2-a]pyridines, emission of it-expanded dyes in protic solvents is usually weaker than in aprotic ones, where they exhibit large Stokes shifts (5500-7000 cm(-1)). Unlike in solution, in the solid state luminescence for benzo[a]imidazo[5,1,2-cd]indolizines is shifted on average by 100 nm relative to the fluorescence of the corresponding imidazo[1,2-a]pyridines, which results in a relatively strong (Phi(ft) = 0.18 to 0.27) emission of the red light. Benzolalimidazo[5,1,2-cd]indolizines possessing a methoxy substituent have much higher fluorescence quantum yields than analogues bearing fluorine and methyl substituents. (literal)
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