Journal of Organic Chemistry p. 1475 - 1480 (2008)
Update date:2022-08-04
Topics:
De La Escosura, Andres
Martinez-Diaz, M. Victoria
Barbera, Joaquin
Torres, Tomas
(Chemical Equation Presented) The use of blends in which a mesogen induces mesomorphism into a non-mesogenic compound has made possible the self-organization of phthalocyanine - [60]fullerene (Pc-C60) dyads into liquid crystals. Pc-C60 dyads 1, 2, or 3, in which two photoactive units are brought together by a phenylenevinylene spacer, have been synthesized through a Heck reaction that links 4-vinylbenzaldehyde to a monoiodophthalocyanine precursor, followed by standard cycloaddition of azomethine ylides - generated from the formylPc derivative and N-methylglycine - to one of the double bonds of C60. The mesomorphic and thermal properties of different mixtures formed by the liquid-crystalline phthalocyanine 4 and dyads 1, 2, or 3 were examined using polarizing optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction (XRD). DSC diagrams of the blends show clear transitions from the crystalline state to a mesophase, and the measured structural parameters obtained from the powder diffraction experiments are consistent with a discotic hexagonal columnar (Colh) structure. Considering that segregation in domains of separated molecules of Pc-C60 dyad and phthalocyanine 4 would preclude mesomorphism due to the mismatch in the column diameter and to the lack of mesogenic character of the pure dyads, a predominance of alternating stacking is proposed. Additionally, the observed decrease in the calculated density of the blend mesophases relative to the mesophase of pure compound 4 is important evidence in this direction.
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Doi:10.1002/anie.200703003
(2008)Doi:10.1021/ja01525a062
(1959)Doi:10.1021/ja005735i
(2001)Doi:10.1016/0022-328X(95)00521-Q
(1995)Doi:10.1021/jo01166a013
(1947)Doi:10.1016/S0040-4039(00)88421-X
(1982)