Microwave-Assisted Synthesis of Phthalocyanine Zinc Complexes Derived from Aminotricyanobiphenyl-Based Azo Dyes

Селиванова, Г. А.; Amosov, E. V.; Vasilyev, Vladimir G.; Luk’yanets, E. A.; Tretyakov, Evgeny V.; Shteingarts, V. D.

doi:10.6060/mhc151192s

Cited by 10 publications

(1 citation statement)

References 21 publications

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“…As can be seen from these examples, it takes a very long time to synthesize the phthalocyanine-based liquid crystals by oil bath heating. Recently, many phthalocyanine compounds have been rapidly synthesized by using microwave heating [6][7][8][9][10][11][12][13][14][15][16][17][18]. However, there have been only two examples of phthalocyanine-based liquid crystals synthesized by microwave heating [17,18], to our best knowledge.…”

Section: Introductionmentioning

confidence: 99%

Discotic liquid crystals of transition metal complexes, 54: Rapid microwave-assisted synthesis and homeotropic alignment of phthalocyanine-based liquid crystals

Akabane

Ohta

Takizawa

et al. 2017

J. Porphyrins Phthalocyanines

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ABSTRACT:The most difficult problem on syntheses of the phthalocyanine-based liquid crystals is the long reaction time. In order to shorten the reaction time, we have developed novel Methods A, B and D, for the syntheses of phthalocyanine-based liquid crystals by using microwave heating and/or adding a phase transfer catalysis of Aliquat 336. A series of phthalocyanine derivatives C n PcZn(1) (n = 10, 12, 14, 16 and 18: a, b, c and e) could be successfully synthesized in a dramatically short reaction time of 30-60 min using Methods A and B by microwave heating. On the other hand, anothor series of the derivatives C n (OH)PcZn (2a-2e) could not be synthesized by microwave heating. Therefore, all these derivatives were synthesized using conventional Method C by oil bath heating, but the reaction took a very long time (22.5-88 h). To shorten the reaction time, we have developed Method D by oil bath heating with adding a phase transfer catalyst of Aliquat 336. In this method, we successfully shortened the reaction time from 88 h to 3 h for the synthesis of the derivative 2a. Thus, the reaction time for oil bath heating can be also greatly shortened by adding the phase transfer catalyst of Aliquat 336. Furthermore, we have established from POM, DSC and temperature-dependent X-ray diffraction measurements that the derivative C 10 PcZn (1a) shows a very rare pseudohexagonal columnar (Col hr ) phase, and that the derivatives C n PcZn (1b-1e) and C n (OH)PcZn (2b-2e) exhibit spontaneous perfect homeotropic alignment in a large area between two glass plates in their Col tet phases.

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