Rational design of near-infrared absorbing organic dyes: Controlling the HOMO-LUMO gap using quantitative molecular orbital theory.

ABSTRACT: Principles are presented for the design of functional near-infrared (NIR) organic dye molecules composed of simple donor (D), spacer (?), and acceptor (A) building blocks in a D-?-A fashion. Quantitative Kohn-Sham molecular orbital analysis enables accurate fine-tuning of the electronic properties of the ?-conjugated aromatic cores by effecting their size, including silaaromatics, adding donor and acceptor substituents, and manipulating the D-?-A torsional angle. The trends in HOMO-LUMO gaps of the model dyes correlate with the excitation energies computed with time-dependent density functional theory at CAMY-B3LYP. Design principles could be developed from these analyses, which led to a proof-of-concept linear D-?-A with a strong excited-state intramolecular charge transfer and a NIR absorption at 879 nm. © 2018 The Authors. Journal of Computational Chemistry published by Wiley Periodicals, Inc.

SUBMITTER: Narsaria AK 

PROVIDER: S-EPMC6587560 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature