Novel Series of Diaminoanthraquinone-Based π-Extendable Building Blocks with Tunable Optoelectronic Properties

Ganesh Masilamani; Harikrishna Batchu; Dana Amsallem; Anjan Bedi

doi:10.1021/acsomega.2c03609

Novel Series of Diaminoanthraquinone-Based π-Extendable Building Blocks with Tunable Optoelectronic Properties

ACS Omega. 2022 Jul 13;7(29):25874-25880. doi: 10.1021/acsomega.2c03609. eCollection 2022 Jul 26.

Authors

Ganesh Masilamani¹, Harikrishna Batchu², Dana Amsallem², Anjan Bedi¹

Affiliations

¹ Department of Chemistry, SRM Institute of Science and Technology, Kattankulathur, Chennai 603203, India.
² Institute of Chemistry, The Hebrew University of Jerusalem, Edmond J. Safra Campus, Jerusalem 91904, Israel.

Abstract

We have achieved the first series of DAAQ-based building blocks, viz., n -TIPS-DAAQs (n = 1-4), and unraveled a rational design of their π-extension. Sequentially increasing numbers (n) of the exocyclic π-linkers showed (a) a systematic bathochromic shift in both absorption and emission spectra, (b) selective stabilization of the lowest-unoccupied molecular orbital (LUMO), and (c) unselective changes in the S₀/S₁ states. To our surprise, the LUMO level of 4-TIPS-DAAQ (-3.72 eV) was found to be comparable to that of PC₆₀BM.