Syntheses and properties of five-ring fused azo- and thio-aromatic compounds containing imide substituent was written by Yang, Ning;Qiao, Xiaolan;Fang, Renren;Tao, Jingwei;Hao, Jian;Li, Hongxiang. And the article was included in Huaxue Xuebao in 2016.Synthetic Route of C8H7BO2S This article mentions the following:
Five-ring fused azo- and thio-aromatic compounds 1 and 2 containing imide substituent were designed and synthesized. 3,4-Dibromo-1-(2-ethylhexyl)-1H-pyrrole-2,5-dione reacted with lithium indyl and benzothiophene-3-boronic acid resp., affording intermediates 3 and 4. Compound 3 was intramol. cyclized in the presence of PdCl2 to give target compound 1. And compound 2 was prepared through intramol. cyclization of intermediate 4 by means of photochem. ring closure reaction and oxidation The physicochem. properties of compounds 1 and 2 were thoroughly investigated with TGA, UV-vis absorption spectra and cyclic voltammetry. Exptl. results showed the introduction of imide substituent not only increased the solubility of compounds 1 and 2, but also decreased their energy levels of the HOMO (HOMO) and the LUMO (LUMO). The HOMO/LUMO energy levels of compounds 1 and 2 are -5.58/-2.25 eV -6.04/-3.51 eV resp. Single crystals of compound 1 were grown through solvent evaporation method in the mixture of dichloromethane and petroleum ether. Single crystal structure revealed compound 1 has a planar conjugated core and forms dimmer in the crystal. Strong π-π intermol. interactions exist in the dimmer, and hydrogen bonds (NH···O=C) are observed among dimmers. The charge carrier mobilities of compounds 1 and 2 were investigated through thin film transistors. The transistors were fabricated with top-contact/bottom-gate device configurations. And thin films were deposited in vacuum on octadecyltrichlorosilane (OTS)-modified Si/SiO2 substrates. Transistors performance of compound 2 displays obvious p-type performance with a mobility of 2.75 × 10-3 cm2·V-1·s-1. However, compound 1 exhibited no organic field-effect transistor (OFET) behavior. In order to understand the different device performances of compounds 1 and 2, their thin films were investigated by at. force microscopy (AFM) and X-ray diffraction (XRD). AFM images showed that compound 1 formed continuous thin film with small size of microstructures, the existence of grain boundaries hindered the transport of charge carriers in the film. XRD curves revealed that compound 2 formed crystalline thin films. Through the continuity of 2 films was worse than that of 1, the large size of microstructures and the crystalline property of the films facilitated the transport of charge carriers. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6Synthetic Route of C8H7BO2S).
Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. It is also used in the manufacturing of dyes such as thioindigo.Synthetic Route of C8H7BO2S
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem