1,2,5,6,9-Pentaazacoronenes (PACs) and π-Extended PAC Derivatives: Synthesis, Crystal Structure, and Optical and Redox Properties

Yixun Sun; Tian Yang; Chong Chen; Bo Yang; Yihui Yang; Jing Li; Huaming Sun; Junfa Wei

doi:10.1021/acs.orglett.1c01574

1,2,5,6,9-Pentaazacoronenes (PACs) and π-Extended PAC Derivatives: Synthesis, Crystal Structure, and Optical and Redox Properties

Org Lett. 2021 Aug 6;23(15):5616-5620. doi: 10.1021/acs.orglett.1c01574. Epub 2021 Jun 18.

Authors

Yixun Sun¹, Tian Yang¹, Chong Chen¹, Bo Yang¹, Yihui Yang¹, Jing Li¹, Huaming Sun¹, Junfa Wei¹

Affiliation

¹ Key Laboratory of Applied Surface and Colloid Chemistry (Ministry of Education), Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, P. R. China.

PMID: 34142840
DOI: 10.1021/acs.orglett.1c01574

Abstract

A novel class of 1,2,5,6,9-pentaazacoronene (PAC, 1) derivatives and π-extended PAC derivatives, chromeno[2,3,4-ij]pentaazacoronenes (CPACs, 2), has been successfully synthesized on the basis of intramolecular diazo-coupling reaction and Pictet-Spengler cyclization. Single-crystal analysis demonstrates that 1o (R¹ = H) displays a herringbone packing motif while 1s (R¹ = C₃F₇) packs into an S-shaped arrangement. Photophysical and electrochemical studies indicated that the new PAC system manifested significantly red-shifted absorption and emission capacity, larger Stokes shifts, and narrower HOMO-LUMO energy gaps.