Panchromatic Absorption of Unsymmetrical Donor-Acceptor Dyes Based on a Meta-Conjugated 1,3,5-Heteroaryltriazine Core

Authors

• Jacob G. Rothera, University of Windsor
• Hi Taing, University of Windsor
• Menandro Cruz, University of Windsor
• Anton Dmitrienko, University of Windsor
• V. Nicholas Vukotic, University of Windsor
• Sean M. Ryno, University of Kentucky
• Chad Risko, University of KentuckyFollow
• A. Mohan Raj, University of Montreal
• William G. Skene, University of Montreal
• S. Holger Eichhorn, University of WindsorFollow

Abstract

Attachment of three different heterocycles with electron donor or acceptor character to a central 1,3,5-triazine core generates readily soluble side-chain free dyes with two displaying soft crystalline mesomorphism and one displaying a nematic liquid crystal phase as confirmed by polarized optical microscopy, calorimetry, gravimetric analysis, and powder X-ray diffraction. Equally intriguing is the dyes’ relatively strong electronic communication between donor and acceptor subchromophores that are meta-conjugated to one another, which is experimentally observed as a broad intramolecular charge-transfer absorption that can extend over 100 nm past the most intense absorption event and is computationally confirmed through density functional theory (DFT) evaluations of the molecular ground- and excited-state properties. This molecular design permits the preparation of dyes with panchromatic absorption not just based on the additive absorption of individual subchromophores.

Document Type

Article

Publication Date

2-20-2025

Notes/Citation Information

Publisher Copyright: © 2025 Wiley-VCH GmbH.

Digital Object Identifier (DOI)

10.1002/chem.202403860

Archival?

Archival

Repository Citation

Rothera, Jacob G.; Taing, Hi; Cruz, Menandro; Dmitrienko, Anton; Vukotic, V. Nicholas; Ryno, Sean M.; Risko, Chad; Mohan Raj, A.; Skene, William G.; and Eichhorn, S. Holger, "Panchromatic Absorption of Unsymmetrical Donor-Acceptor Dyes Based on a Meta-Conjugated 1,3,5-Heteroaryltriazine Core" (2025). Chemistry Faculty Publications. 251.
https://uknowledge.uky.edu/chemistry_facpub/251