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Orłowski, Rafał,Banasiewicz, Marzena,Clermont, Guillaume,Castet, Fré,dé,ric,Nazir, Rashid,Blanchard-Desce, Mireille,Gryko, Daniel T. The Royal Society of Chemistry 2015 Physical chemistry chemical physics Vol.17 No.37
<P>We describe the design, synthesis, and fluorescent profile of two environment-sensitive dyes in which an electron-donating group is conjugated to an electron-accepting unit <I>via</I> a pyrrolo[3,2-<I>b</I>]pyrrole ring system. The maximum emission wavelength (<I>λ</I><SUB>em</SUB>) of these donor–donor–acceptor (D–D–A) pyrrolo[3,2-<I>b</I>]pyrroles was found to be very sensitive to the environment (a bathochromic shift of about 100 nm in polar solvents). The longer emission wavelength in polar aprotic as well as hydrophilic solvents compared with that in low-polarity hydrophobic solvents was due to an ICT character of the excited state. The Stokes shift increased in both cases following the polarity differences, reaching ∼7000 cm<SUP>−1</SUP> in MeOH for the compound possessing a cyano group and dimethylamino groups at the periphery. Interestingly, the two-photon absorption responses were also found to be quite sensitive to solvent polarity with an increase by a factor of about 2 on going from an apolar solvent to a highly polar protic or aprotic solvent.</P> <P>Graphic Abstract</P><P>The pyrrolo[3,2-<I>b</I>]pyrrole core was determined to be an efficient linker allowing the conjugation of peripheral benzene rings. The resulting dipolar compounds displayed strong solvatochromism of fluorescence. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c5cp03523f'> </P>