Abstract

Designing and synthesizing nonlinear optical materials with excellent performance has always been a persistent goal pursued by material chemists. In paper, based on the reported [6]heliceno-bis(naphthalimides) 2, four new molecules are designed by introducing 2-dicyanomethylene-1,3-dithiole on the two middle benzene rings of the naphthalimide unit and replacing CH3 units on the R1 and R2 substituents with NH2/NO2 moieties, or their combination. The electronic spectra, reorganization energy and second-order nonlinear optical properties of the reported derivatives 1 and 2, as well as four newly designed derivatives, have been systematically investigated by means of (time-dependent) density functional theory calculations. Frontier molecular orbital analysis, electron excitation analysis, reorganization energy, and the calculation of the static and dynamic first hyperpolarizability all indicate that the studied system is greatly influenced by the number of benzene rings in helicene core and the terminal substituents attached at both ends of helicene core. Further analysis of depolarization, hyperpolarizability density and unit sphere representation reveals the nature of the nonlinear optical response of the studied system. Considering that the studied derivatives all have large static first hyperpolarizabilities (e.g., 210 × 10-30 esu for derivative 5) and small reorganization energy (e.g., 0.092 eV of hole reorganization energy and 0.118 eV of electron reorganization energy for derivative 3), they are expected to become potential nonlinear optical materials with excellent performance and bipolar transport materials. This work contributes to the rational design of high-performance molecules based on [n]helicenes derivatives and further explores their potential applications in optical materials.

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