Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 33, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202205658
Keywords
Acid-Responsive Luminescence; Azulene; Nonalternant Isomers; Organic Electronics; Polycyclic Aromatic Hydrocarbons
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Funding
- National Natural Science Foundation of China [21971211, 22171232]
- Natural Science Foundation of Zhejiang Province [2022XHSJJ007]
- Qiantang River Talent Foundation [QJD1902029]
- Westlake University
- Instrumentation and Service Center for Molecular Science
- Instrumentation and Service Center for Physical Science
- Westlake University HPC Center
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A new modular approach for the synthesis of various azulene compounds with narrow band gaps and high stability has been developed, showing enhanced near-infrared fluorescence.
A modular approach to azulene building blocks was developed starting from readily available aryl-substituted cyclopentadiene and ortho-haloaryl aldehyde by dehydration condensation followed by palladium-catalyzed C-H coupling. It facilitates the synthesis of four nonalternant isomers of pentacene and hexacene, namely, dibenzo[e,g]azulene, benzo[1,2-f : 5,4-f ']diazulene, benzo[1,2-f : 4,5-f ']diazulene, and naphtho[2,3-f : 6,7-f ']diazulene, which exhibit narrow band gaps with high stability in addition to protonation-caused enhanced near-infrared fluorescence. We discovered that in these isomers, i) constitutional isomerism influences significantly their photoelectric properties and (i) the elongation of the conjugation system does not necessarily lead to a narrowing in the band gap. Due to the easy modifiability of the nonazulene building blocks, this strategy can be extended to modularly prepare numerous multiazulene-fused aromatics.
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