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Volumn 14, Issue 36, 2008, Pages 11343-11357

Control of H- and J-type π stacking by peripheral alkyl chains and self-sorting phenomena in perylene bisimide homo- and heteroaggregates

Author keywords

Dyes pigments; Organogelators; Self assembly; Systems chemistry; Vortex effect

Indexed keywords

ABERRATIONS; ALKYLATION; AMIDES; CHROMOPHORES; CIRCULAR DICHROISM SPECTROSCOPY; COAGULATION; COLLOIDS; DATA STORAGE EQUIPMENT; DICHROISM; ELECTRON TRANSITIONS; GELATION; GELS; HYDROGEN; HYDROGEN BONDS; OPTICAL PROPERTIES; SELF ASSEMBLY; SPECTROSCOPIC ANALYSIS; VORTEX FLOW;

EID: 57649195280     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801454     Document Type: Article
Times cited : (434)

References (122)
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    • Remarkably similar structures have been obtained from very different building block, see : L.-s. Li, H. Jiang, B. W. Messmore, S. R. Bull, S. Stupp, Angew. Chem. 2007, 119, 5977;
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    • For a recent review on chiral supramolecular aggregates, see: A. R. A. Palmans, E. W. Meijer, Angew. Chem. 2007, 119, 9106;
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    • Even at a 20 % incorporation of the chiral PBI-3 in a H-type stack of achiral PBI-1, the CD signal intensity is almost saturated due to the sergeant-and-soldier principle. For few recent examples on such chiral amplifications in other supramolecular assemblies, see: a A. Lohr, F. Würthner, Chem. Commun. 2008, 2227;
    • Even at a 20 % incorporation of the chiral PBI-3 in a H-type stack of achiral PBI-1, the CD signal intensity is almost saturated due to the "sergeant-and-soldier" principle. For few recent examples on such chiral amplifications in other supramolecular assemblies, see: a) A. Lohr, F. Würthner, Chem. Commun. 2008, 2227;
  • 105
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    • Although CD spectroscopic studies revealed a preferential population of one-handed helices in chiral solvent, AFM images of the gels made in (R)-limonene were found to consist of both types of helices. It should be noted that gelation is a very fast process, which occurs at a much higher chromophore concentration than the solution chiroptical studies. Thus, the chiral induction from external sources may not be adequate in effectively populating only one-handed helices. Even PBI-6, which has one chiral alkyl group as a peripheral substituent, forms both handed helices, which indicates a weak influence of the remote chiral center in the alkyl side chain on the chromophore packing in the fast gelation process. However, in PBI-3, in which all of the three alkyl substituents are chiral, only P-type helices were found in AFM studies
    • Although CD spectroscopic studies revealed a preferential population of one-handed helices in chiral solvent, AFM images of the gels made in (R)-limonene were found to consist of both types of helices. It should be noted that gelation is a very fast process, which occurs at a much higher chromophore concentration than the solution chiroptical studies. Thus, the chiral induction from external sources may not be adequate in effectively populating only one-handed helices. Even PBI-6, which has one chiral alkyl group as a peripheral substituent, forms both handed helices, which indicates a weak influence of the remote chiral center in the alkyl side chain on the chromophore packing in the fast gelation process. However, in PBI-3, in which all of the three alkyl substituents are chiral, only P-type helices were found in AFM studies.
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    • For J-type π stacking of PBI dyes in the solid state, see: a
    • For J-type π stacking of PBI dyes in the solid state, see: a) F. Gräser, E. Hädicke, Liebigs Ann. Chem. 1984, 483;
    • (1984) Liebigs Ann. Chem , pp. 483
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    • For recent examples of J-aggregating PBI chromophores, see: a
    • For recent examples of J-aggregating PBI chromophores, see: a) T. E. Kaiser, H. Wang, V. Stepanenko, F. Würthner, Angew. Chem. 2007, 119, 5637;
    • (2007) Angew. Chem , vol.119 , pp. 5637
    • Kaiser, T.E.1    Wang, H.2    Stepanenko, V.3    Würthner, F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.