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Nowak-Kró,l, Agnieszka,Fimmel, Benjamin,Son, Minjung,Kim, Dongho,Wü,rthner, Frank The Royal Society of Chemistry 2015 Faraday discussions Vol.185 No.-
<P>Foldamer systems comprised of two perylene bisimide (PBI) dyes attached to the conjugated backbones of 1,2-bis(phenylethynyl)benzene and phenylethynyl-bis(phenylene)indane, respectively, were synthesized and investigated with regard to their solvent-dependent properties. UV/Vis absorption and steady-state fluorescence spectra show that both foldamers exist predominantly in a folded H-aggregated state consisting of π–π-stacked PBIs in THF and in more random conformations with weaker excitonic coupling between the PBIs in chloroform. Time-resolved fluorescence spectroscopy and transient absorption spectroscopy reveal entirely different relaxation pathways for the photoexcited molecules in the given solvents, <I>i.e.</I> photoinduced electron transfer leading to charge separated states for the open conformations (in chloroform) and relaxation into excimer states with red-shifted emission for the stacked conformations (in THF). Supported by redox data from cyclic voltammetry and Rehm–Weller analysis we could relate the processes occurring in these solution-phase model systems to the elementary processes in organic solar cells. Accordingly, only if relaxation pathways such as excimer formation are strictly avoided in molecular semiconductor materials, excitons may diffuse over larger distances to the heterojunction interface and produce photocurrent <I>via</I> the formation of electron/hole pairs by photoinduced electron transfer.</P>
Jeong, Seung-Doo,Nowak-Kró,l, Agnieszka,Kim, Youngmee,Kim, Sung-Jin,Gryko, Daniel T.,Lee, Chang-Hee Royal Society of Chemistry 2010 Chemical communications Vol.46 No.46
<P><I>meso</I>-Alkylidene (<I>m</I>-benzi)pentaphyrin containing exocyclic C&z.dbd;C double bonds at two <I>meso</I>-positions is synthesized and fully characterized for the first time. The single crystal X-ray crystallographic analysis shows a concave conformation with two pyrrole rings inverted. The first protonation occurs exclusively at core nitrogen. The synthesized compound displays concentration dependent chromogenic responses for fluoride anion in organic solvent.</P> <P>Graphic Abstract</P><P><I>meso</I>-Alkylidene (<I>m</I>-benzi)pentaphyrin containing exocyclic C&z.dbd;C double bonds at two <I>meso</I>-positions is synthesized and fully characterized for the first time. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c0cc03263h'> </P>