Donor-acceptor columnar liquid crystals (DACLCs) are a class of supramolecular organic materials consisting of two molecular components: an electron-poor aromatic (acceptor) and an electron-rich aromatic (donor). In this work, we explore the synthesis of new, highly substituted 2,3,6,7-tetrahydroxy-anthracenes and anthraquinones as functional donor and/or acceptor components that can π-stack and bind cations in a new class of hybrid DACLCs. First, the synthesis of several derivative molecules and their incorporation into DACLCs will be presented. Briefly, 1,2-Dimethoxybenzene (veratrole) is condensed with various aldehydes (OCH-R) to afford several 2,3,6,7-tetramethoxy-9,10-(R)-anthracenes. Derivatives where R is an alkyl chain of butyl or longer with be demethylated to form a series of the highly electron-rich 2,3,6,7-tetrahydroxy-9,10-(R)-anthracenes. In the case where R= methyl (reaction with acetaldehyde), the corresponding anthracene product is converted to the 2,3,6,7-tetramethoxy-anthraquinone according to literature procedures, followed by demethylation to form 2,3,6,7-tetrahydroxy-anthraquinone. Incorporation of these synthesized derivatives and their characterization as components of new DACLCs will be discussed. Finally, initial experiments on the formation of hybrid DACLCs made via the chelation of Zn2+ and other multi-valent cations to the ortho-dihydroxy groups of the 2,3,6,7-tetrahydroxy-anthracene and anthraquinone components will be discussed.

Hybrid donor-acceptor columnar liquid crystals based on 2,3,6,7-tetrahydroxy-anthracenes and anthraquinones

Where thousands of chemistry professionals meet to share ideas and advance scientific and technical knowledge. Spring 2023 abstracts, posters, and presentations will launch at the end of March.

ACS Spring 2023

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.