A synthetic pathway to macrocyclic and optically active pentamethinium salts

Payrastre, Corinne; Obaya, Nicaise; Madaule, Yves; Wolf, J. G.

doi:10.1016/s0040-4039(00)76827-4

Cited by 29 publications

(2 citation statements)

References 3 publications

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“…Other synthetic methods leading to the same compound were recently developed in our group (Madaule, Ramarohetra & Wolf, 1992;Payrastre, Obaya, Madaule & Wolf, 1994). See Table 1 for full experimental details.…”

Section: Methodsmentioning

confidence: 99%

Structure of 1,5-bis(dimethylamino)-1,5-diphenylpentadienylium perchlorate and modelling of pentadienylium salts (cyanine dyes)

Declercq¹,

Dubourg²,

Payrastre³

et al. 1996

Acta Crystallogr Sect B

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C21H25N2+.CIO4 -(orange crystals), Mr = 404.9, orthorhombic; P212121, a = 7.810(2), b = 15.007(3), c = 18.326 (3)/~, V = 2147.8 (7)/~3. Graphitemonochromated Mo Kc~ source at room temperature; A = 0.71069A,, /z = 0.22 mm -l, Z = 4; F(000) = 856, Dx = 1.25 g cm -3, R = 0.057 for 1392 independent data. As for the unsubstituted pentamethinium dyes, the chain lies in an all-trans planar configuration. Molecular modelling calculations reproduce the Xray structure with good accuracy, even in the case of more crowded pentadienylium cations, i.e. 1,5-bis(dimethylamino)-1,3,5-triphenylpentadienylium perchlorate.

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Section: Methodsmentioning

confidence: 99%

Structure of 1,5-bis(dimethylamino)-1,5-diphenylpentadienylium perchlorate and modelling of pentadienylium salts (cyanine dyes)

Declercq¹,

Dubourg²,

Payrastre³

et al. 1996

Acta Crystallogr Sect B

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“…[17] Further work on inherently chiral polymethine dyes has also been done recently by Grahn et al, [22] Wolf et al, [23] and particularly Buß et al [24Ϫ30] The observation by Dähne, Kirstein, et al, [31Ϫ34] that achiral trimethinium cyanine dyes with long N-alkyl groups spontaneously form chiral J-aggregates with optical activity in solution should also be mentioned in this context.…”

Section: Introductionmentioning

confidence: 96%

Syntheses, Absolute Configurations, and UV/Vis Spectroscopic Properties of New Chiral Tri- and Pentamethinium Streptocyanine Dyes with 4-Aminophenyl 4-Methylphenyl Sulfoxide Endgroups

Reichardt¹,

Erfurt²,

Harms³

et al. 2002

Eur. J. Org. Chem.

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Keywords: Chirality / Cyanines / Dyes / Polymethines / UV/Vis spectroscopyStarting with monochiral 4-aminophenyl 4-methylphenyl sulfoxides 3a and 3b, the absolute configurations of which were determined by X-ray analysis, we have synthesized the new chiral C 2 -symmetrical tri-and pentamethinium streptocyanine dyes 5a and 5b and 7a and 7b with sulfinyl groups as stereogenic centers in the two endgroups. Deprotonation of the trimethinium dyes 5a and 5b gave the intramolecularly H-bonded neutral streptocyanines 6a and 6b; the molecular

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