147699-64-7Relevant academic research and scientific papers
Flying-seed-like liquid crystals. Part 4: A novel series of bulky substituents inducing mesomorphism instead of using long alkyl chains
Yoshioka, Miho,Ohta, Kazuchika,Yasutake, Mikio
, p. 13828 - 13839 (2015)
We synthesized a novel series of flying-seed-like derivatives (3a-g) based on phthalocyaninato copper(ii) (abbreviated as PcCu) substituted by bulky groups {PhO (a), (o-C1)PhO (b), (m-C1)PhO (c), (p-C1)PhO (d), [m,p-(C1)2]PhO (e), [m,m′-(C1)2]PhO (f), and [m,p,m′-(C1)3]PhO (g)} instead of using long alkyl chains, in order to investigate their mesomorphism. Their phase transition behaviour and the mesophase structures were established using a polarizing optical microscope, a differential scanning calorimeter, a thermogravimetry analyser and a temperature-dependent small angle X-ray diffractometer. It was demonstrated that (PhO)8PcCu (3a) and [(p-C1)PhO]8PcCu (3d) show no mesophase, whereas [(m-C1)PhO]8PcCu (3c), {[m,p-(C1)2]PhO}8PcCu (3e), {[m,m′-(C1)2]PhO}8PcCu (3f), and {[m,p,m′-(C1)3]PhO}8PcCu (3g) show various kinds of columnar mesophases of Colro(P21/a), Colro(P21/a), Colro(C2/m) and Coltet.o, respectively, while [(o-C1)PhO]8PcCu (3b) shows a monotropic Colro(P2m) mesophase. Thus, we revealed that mesomorphism could be induced by these novel bulky substituents instead of using long alkyl chains, and that the mesophase structures were greatly affected by the number and position of the methoxy groups. In particular, it is very interesting that the derivatives with methoxy group(s) at the meta position(s), namely, 3c, 3e, 3f and 3g, tend to show enantiotropic mesophase(s), whereas neither the derivative with no methoxy group, 3a, nor the derivative with a methoxy group at the para position, 3d, show a mesophase. This journal is
A simple synthesis of 4,5-disubstituted 1,2-dicyanobenzenes and 2,3,9,10,16,17,23,24-octasubstituted phthalocyanines
Wohrle,Eskes,Shigehara,Yamada
, p. 194 - 196 (2007/10/02)
4,5-Dichloro-1,2-dicyanobenzene (5) was prepared in an overall yield of 49% from 4,5-dichloro-1,2-benzenedicarboxylic acid (1). The reactions of 5 with phenols, thiophenol and 1-propanethiol led in a nucleophilic displacement reaction to the 4,5-bis(aryloxy)-, 4,5-bis(phenylthio)- and 4,5-bis(propylthio)-1,2-dicyanobenzenes 6 which were converted in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene in high yields to octasubstituted phthalocyanines (tetrabenzoporphyrazines) 7. Some compounds 7 contain eight free phenolic, carboxylic acid or pyridyl groups.
