Jin, Ke;Huang, Yuhui;Feng, Yudi;Guo, Jia;Xu, Jiangtao;Wang, Changchun published 《Soluble, Thermally Stable, and Low Thermal Expansion Polyarylamides Enabled by a Seven-Membered Carbocycle》. The research results were published in《ACS Applied Polymer Materials》 in 2020.Computed Properties of C12H12N2O The article conveys some information:
Soluble, thermally, and dimensionally stable polyarylamides have been a long-standing challenge for polymer chemists and materials scientists. Herein, we designed and synthesized a series of polyarylamides with various contents of the seven-membered carbocycle unit of 1,2:4,5-dibenzocycloheptadiene (DBCHD) as the linkage in the polymer backbones. In comparison to their analog with an ether linkage, these advanced polyarylamides showed improved thermal stability (5% weight loss temperature, 413-480°) and elevated glass transition temperatures (218-243°) depending on the content of the DBCHD unit. Given the good solubility in polar aprotic solvents, the polyarylamide films were prepared by simple and straightforward solution casting, which presented excellent optical transparency and low coefficient of thermal expansion (CTE). The polyarylamide with the highest content of DBCHD (43.5 wt %) showed a CTE value of 41.0 ppm/K in the temperature range of 0-150°, which is 43% lower than that of the corresponding ether-linked polyarylamide film. Variable-temperature 1H NMR demonstrated that the nonplanar and moderately rigid structural features of DBCHD units in polymer backbones are the key influence factors that contribute to thermal stability and reduced thermal expansion. To complete the study, the researchers used 3-(4-Aminophenoxy)aniline (cas: 2657-87-6) .
3-(4-Aminophenoxy)aniline is one of ethers-buliding-blocks. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. Computed Properties of C12H12N2O The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.
Reference:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem