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Volumn 16, Issue 25, 2010, Pages 7380-7384

Chiral self-recognition and self-discrimination of strapped perylene bisimides by π-stacking dimerization

Author keywords

Chiral recognition; Dyes pigments; Homochirality; Pi interactions; Self assembly

Indexed keywords

CHEMICAL EQUATIONS; CHIRAL AUXILIARIES; CHIRAL RECOGNITION; CONFIGURATIONALLY; DYES/PIGMENTS; ENANTIOMERIC RATIO; H NMR SPECTROSCOPY; HOMOCHIRAL DIMERS; HOMOCHIRALITY; PERYLENE BISIMIDE DYE; PERYLENE BISIMIDES; PI INTERACTIONS; SELF-RECOGNITION;

EID: 77954079626     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001137     Document Type: Article
Times cited : (65)

References (61)
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    • For a general review on perylene bisimides and their supramolecular architectures, see: a) F. Würthner, Chem. Commun. 2004, 1564-1579;
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    • [17] However, this situation holds only true if achiral dyes are stacked in a helical fashion. Here, the different amplitudes of the positive and negative parts of the bisignated CD couplets might arise from the intrinsic molecular chirality of these twisted PBIs (see: V. Büß, C. Reichardt, Chem. Commun. 1992, 1636-1638).
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    • Büß, V.1    Reichardt, C.2
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    • note
    • Evidently, in the case of (rac)-2b more than two species are involved due to the possibility of homo- and heterochiral dimers formation. Thus, the dimerization process is either highly stereoselective or both dimers exhibit almost identical UV/Vis absorption spectra.
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    • note
    • -2M concentration in n-hexane. On the basis of the measured colligative concentrations, aggregation numbers N of 2.5 and 2.3 are estimated for (rac)-2b and (P)-2b, respectively. These data again corroborate the formation of dimers in self-assembly of PBIs 2b.
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    • note
    • To exclude concentration effects as a possible reason for the different chemical shifts of the aromatic protons of (rac)-2b and (P)-2b (or (M)-2b), a double-concentrated solution of (rac)-2b was measured relative to that of (P)-2b (or (M)-2b).
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    • This interesting self-discrimination of enantiomers in the absence of chiral auxiliaries has also been reported for dimer complexes involving metal coordination and hydrogen bonding: a) T. Williams, R. G. Pitcher, P. Bommer, J. Gutzwiller, M. Uskoković, J. Am. Chem. Soc. 1969, 91, 1871-1872;
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    • Williams, T.1    Pitcher, R.G.2    Bommer, P.3    Gutzwiller, M.4    Uskoković, J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.