Computational exploration of the structure-photophysical property relationship of 2,6-dicyanoaniline derivatives for optoelectronic applications

Abstract

Design and development of 2,6-Dicyanoaniline based multifunctional organic molecules with an acceptor-donor-acceptor (A-D-A) framework is gaining momentum in recent years. However, identifying the suitable donor, acceptor and π-linkers remains challenging and necessitates a thorough understanding of the structure-property relationship. In this context, to enhance their properties, two experimentally reported dicyanoaniline (DCA) derivatives are subjected to structural modifications using four electron-releasing groups: OMe, NH2, NHMe, and NMe2, employing density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations. Our findings reveal that all the designed molecules exhibit higher reactivity compared to the reference molecules, with NMe2 showing the most promising attributes, including a lower HOMO-LUMO gap. Percentage contribution analysis reveals that the strength of electron releasing groups significantly alter the stabilization of HOMO. Absorption and emission spectra are obtained from TD-DFT calculations in dimethyl formamide solvent. Moreover, calculations are performed to explore the Nonlinear Optical (NLO) performance of the designed molecules, indicating that all the designed molecules outperform the reference molecules in terms of NLO properties. In summary, this study offers valuable guidance for the development of efficient 2,6-Dicyanoaniline derivatives with great potential for optoelectronic and NLO applications.