Evaluating the Role of Molecular Heredity in the Optical and Electronic Properties of Cross-Conjugated Benzo[1,2-d:4,5-d′]bisoxazoles

A series of eight benzo[1,2-d:4,5-d′]bisoxazole (BBOs) were synthesized using the heredity principle as a design motif, whereby we investigated which characteristics of the linear parents were inherited by their cross-conjugated children. Four linear parents bearing 4-tert-butylbenzene (P) or 1,3-bis(4-tert-butylphenyl)benzene (M) at either the 2,6- or 4,8-position on the BBO and four cross-conjugated children bearing various combinations of the two isoelectronic aryl substituents were evaluated. Due to the bulky nature of the M substituent compared to that of the P substituent, the influence of steric hindrance along the BBO axes was explored theoretically and experimentally. The optical and electronic properties of each molecule…

David L. Wheeler, Alex V. Diodati, Aimée L. Tomlinson, and Malika Jeffries-EL. ACS Omega 2020 5 (21), 12374-12384. DOI: 10.1021/acsomega.0c01126