Theoretical investigation on triphenylamine coelenteramide for bioinspired OLED application using thiophene rings in π-bridge

Jin-Mei Xie; Xiao-Ying Cui; Hongbo Liu; Yan Leng; Chun-Gang Min; Ai-Min Ren

doi:10.1016/j.saa.2023.123324

Theoretical investigation on triphenylamine coelenteramide for bioinspired OLED application using thiophene rings in π-bridge

Spectrochim Acta A Mol Biomol Spectrosc. 2024 Jan 5:304:123324. doi: 10.1016/j.saa.2023.123324. Epub 2023 Sep 1.

Authors

Jin-Mei Xie¹, Xiao-Ying Cui¹, Hongbo Liu², Yan Leng³, Chun-Gang Min⁴, Ai-Min Ren⁵

Affiliations

¹ School of Materials Science and Engineering, Kunming University of Science and Technology, Kunming 650093, PR China.
² College of Information Technology, Jilin Engineering Research Center of Optoelectronic Materials and Devices, Jilin Normal University, Siping 136000, PR China.
³ Faculty of Chemical Engineering, Kunming University of Science and Technology, Kunming 650093, PR China. Electronic address: lengyan@kust.edu.cn.
⁴ Research Center for Analysis and Measurement, Kunming University of Science and Technology, Kunming 650093 PR China. Electronic address: minchungang@kust.edu.cn.
⁵ Institute of Theoretical Chemistry, College of Chemistry, Jilin University, Changchun 130023, PR China. Electronic address: renam@jlu.edu.cn.

PMID: 37678042
DOI: 10.1016/j.saa.2023.123324

Abstract

As light emitter of most marine organisms bioluminescence, coelenteramide (CLM) received much attention due to some exciting application in the field of bioinspired organic light-emitting devices (OLED). Nevertheless, native CLM only emit bright blue light. In order to obtain light of different colors, two CLM analogues, TPA-CLM and TPA-TP-CLM were designed by introduction of triphenylamine group and (thiophene) π-bridge. On the other hand, because the light emitter, CLM was produced by the chemical reaction which originates from the oxidation of bioluminescent substrate, coelenterazine (CLZ), it must be evaluated if and how substituent group tune the chemiluminescent (CL) reaction mechanism, firstly. In this article, the complete chemiluminescent reaction mechanism of TPA-CLZ and TPA-TP-CLZ and the photophysical properties of light emitters, TPA-CLM and TPA-TP-CLM were investigated by (time-dependent) density functional theory, (TD) DFT calculations. The calculations indicate that the introduction of triphenylamine and π-bridge minimally affect the complete reaction process. For the light emitters, TPA-CLM and TPA-TP-CLM, the calculation results indicate that the injection abilities of hole and electron can be largely improved by introduction of triphenylamine and π-bridge. The absorption and emission spectra appeared at longer wavelengths than native CLM. These results illustrate that TPA-CLM and TPA-TP-CLM are good candidates for bioinspired OLED application.

Keywords: Bioinspired organic light-emitting devices; Chemiluminescent mechanism; Coelenterazine; Fluorescence; Time-dependent density functional theory.