Synthesis and chiroptical properties of cyclic anthraquinodimethane dimer using Au-templated method-Reference-Cited by-同舟云学术

Synthesis and chiroptical properties of cyclic anthraquinodimethane dimer using Au-templated method

Published:2024-05-23 Issue:6 Volume:53 Page:
ISSN:0366-7022
Container-title:Chemistry Letters
language:en
Short-container-title:

Author:

Sugiyama Soichiro¹,Murotani Kazuharu²,Ishiwari Fumitaka²^ORCID,Saeki Akinori²^ORCID,Kawai Hidetoshi³^ORCID,Suzuki Takanori¹^ORCID,Tsuchido Yoshitaka³^ORCID,Ishigaki Yusuke¹^ORCID

Affiliation:

1. Department of Chemistry, Faculty of Science, Hokkaido University , N10 W8, North-ward, Sapporo, Hokkaido 060-0810 , Japan

2. Department of Applied Chemistry, Graduate School of Engineering, Osaka University , 2-1 Yamadaoka, Suita, Osaka 565-0871 , Japan

3. Department of Chemistry, Faculty of Science, Tokyo University of Science , 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601 , Japan

Abstract

Abstract Cyclic anthraquinodimethane (AQD) dimer with a highly constrained structure was synthesized by using the Au-templated method. X-ray diffraction analysis and UV–Vis spectroscopy revealed that the AQD skeleton adopts a deeply folded structure and exhibits red-shifted absorptions in the dimer compared to those in noncyclized monomeric AQD. Due to the rigid and constrained structure, both enantiomers of the cyclic AQD dimer with planar chirality can be isolated and show strong circular dichroism signals. It is demonstrated that the Au-templated method is a valuable way to access a highly constrained cyclic structure with AQD skeletons.

Funder

JSPS KAKENHI

JST PRESTO

Publisher

Oxford University Press (OUP)

Link

https://academic.oup.com/chemlett/advance-article-pdf/doi/10.1093/chemle/upae102/57846114/upae102.pdf

Reference28 articles.

1. Linear Monodisperse π-Conjugated Oligomers: Model Compounds for Polymers and More

2. Conjugated Oligomers with Terminal Donor–Acceptor Substitution

3. Designing π-conjugated polymers for organic electronics

4. Bottom-up synthesis of finite models of helical (n,m)-single-wall carbon nanotubes

5. Selective Synthesis of Conjugated Chiral Macrocycles: Sidewall Segments of (−)/(+)‐(12,4) Carbon Nanotubes with Strong Circularly Polarized Luminescence