Ring-Expansion Strategy for α-Aryl Azahelicene Construction: Building Blocks for Optoelectronic Materials

Jia Feng; Limin Wang; Xiaoping Xue; Zengyin Chao; Biqiong Hong; Zhenhua Gu

doi:10.1021/acs.orglett.1c03070

Ring-Expansion Strategy for α-Aryl Azahelicene Construction: Building Blocks for Optoelectronic Materials

Org Lett. 2021 Oct 15;23(20):8056-8061. doi: 10.1021/acs.orglett.1c03070. Epub 2021 Oct 5.

Authors

Jia Feng¹, Limin Wang¹, Xiaoping Xue¹, Zengyin Chao¹, Biqiong Hong², Zhenhua Gu^{1

2}

Affiliations

¹ Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, People's Republic of China.
² College of Materials and Chemical Engineering, Minjiang University, Fuzhou, Fujian 350108, People's Republic of China.

PMID: 34609885
DOI: 10.1021/acs.orglett.1c03070

Abstract

An acid-mediated rapid synthesis of α-aryl azahelicenes via C-C bond cleavage of helical 9H-fluoren-9-ols is reported. The newly introduced aryl ring and pyridine moieties provide an excellent opportunity to further tune the properties of azahelicences: i.e., photoluminescence. The novel α-aryl azahelicenes showcase high circularly polarized luminescence (CPL) efficiencies (4.5 × 10^-3) as well as CPL brightness (B_CPL), reaching 7.39 M^-1 cm^-1, which indicates a potential application as chiral emitters.