Discotic liquid crystals of transition metal complexes 29: mesomorphism and charge transport properties of alkylthio-substituted phthalocyanine rare-earth metal sandwich complexes

Ban, Kazue; Nishizawa, Kaori; Ohta, Kazuchika; Craats, A.M. van de; Warman, John M.; Yamamoto, Iwao; Shirai, Hirofusa

doi:10.1039/b003984p

Cited by 133 publications

(92 citation statements)

References 14 publications

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“…In this case, Peak No. 1 corresponds to an overlapped reflection from both (110) and (200) planes of a rectangular lattice, for which we have a unique relationship, a r = √3 b r , between the rectangular lattice constants (a r and b r ; a r > b r ) [20]. In such a relationship, all the observed spacing values of Peak Nos.…”

Section: Spontaneous Perfect Homeotropic Alignmentmentioning

confidence: 98%

“…As can be seen from this table, each of the derivatives 1a-1e shows a crystal phase (K) at room temperature (rt). When the K phase of 1a was heated from rt, it transformed into a very rare pseudohexagonal (hexagonal-rectangular) columnar (Col hr ) mesophase [20] at 112.8 °C. In the other derivatives 1b-1e, the K phase transformed into a usual hexagonal columnar (Col h ) mesophase.…”

Section: Phase Transition Behaviormentioning

confidence: 99%

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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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Section: Spontaneous Perfect Homeotropic Alignmentmentioning

confidence: 98%

Section: Phase Transition Behaviormentioning

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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“…The terminal OH group in 5 was esterified with pformyl benzoic acid by Steglich reaction to afford [m, p, m'-(C 14 O) 3 PhO] 6 PcCu-OFBA (6). Finally, the target Pc-C 60 dyad, [m, p, m'-(C 14 O) 3 PhO] 6 PcCu-C 60 (7), was synthesized from 6 with N-methylglycine and fullerene by Prato reaction. These synthetic methods for the Pc derivatives (5-7) were a little bit modified our previously reported ones [37].…”

Section: Experimental Synthesismentioning

confidence: 99%

“…Figure S1. MALDI-TOFF mass spectra of the Pc-C 60 dyad, [m, p, m'-(C 14 O) 3 PhO] 6 PcCu-C 60 (7). The spectra were measured in positive ion reflector mode using 2, 5-dihydroxybenzoic acid as the matrix.…”

Section: Columnar Structuresmentioning

confidence: 99%