Journal
ORGANIC LETTERS
Volume 23, Issue 15, Pages 5616-5620Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01574
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Funding
- National Natural Science Foundation of China [21572124, 21272145, 21602128, 21702131, 21871169]
- Natural Science Basic Research Plan in Shaanxi Province of China [2016ZDJC-03, 2017JQ2010]
- Fundamental Research Funds for the Central Universities [SNNU. 2019TS040]
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The novel PAC derivatives and CPACs exhibit significantly red-shifted absorption and emission capacity, larger Stokes shifts, and narrower HOMO-LUMO energy gaps.
A novel class of 1,2,5,6,9-pentaazacoronene (PAC, 1) derivatives and p-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 (R-1 = H) displays a herringbone packing motif while 1s (R-1 = 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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