1,2,5,6,9-Pentaazacoronenes (PACs) and π-Extended PAC Derivatives: Synthesis, Crystal Structure, and Optical and
Yixun Sun1, Tian Yang1, Chong Chen1
1Key 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.
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.
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