Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
Author ORCID Identifier
Abstract
Here, we report improved syntheses, detailed characterizations and reactions of a series of acene-2,3- dicarbaldehydes including tetracene-2,3-dicarbaldehyde. DFT calculations corroborate and complement the experimental results. Tetracene-2,3-dicarbaldehyde and the benchmark organic semiconductor pentacene have isoelectronic p-systems and similar HOMO–LUMO gaps. Tetracene-2,3-dicarbaldehyde is soluble in a host of organic solvents (e.g., DMF, toluene, THF, chloroform, dichloromethane) and shows excellent photooxidative resistance in solution phases exposed to light and air. Further, it is readily sublimed from the solid-state without decomposition, and can be functionalized using different chemistries. We have demonstrated the utility of acene-2,3-dicarbaldehydes as reactants in the syntheses of novel diaryl-2,3-acenedimethanols and acenotropones via Grignard reactions and double-aldol condensation reactions, respectively. The acenotropones were further reacted with concentrated H2SO4 to generate hydroxyacenotropylium ions that exhibit long wavelength absorption in the visible and near-IR regions. The optical gap measured for hydroxyanthracenotropylium ion is 1.3 eV. The results gained here implicate acene-2,3-dicarbaldehydes as potential high-value organic semiconductors and as precursors to a host of interesting molecules and materials.
Date Created
October 2, 2024
Department
Chemistry
Publication Date
Summer 8-9-2024
Subject
highly conjugated, low band gap organic semiconductor
Journal Title
RSC Advances
Language
English
Publisher
Royal Society of Chemistry
Digital Object Identifier (DOI)
10.1039/D4RA04273E
Document Type
Article
Recommended Citation
RSC Adv., 2024, 14, 25008