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Curved π-Conjugated Dehydrobenzoannulene as an Electron Acceptor Enabling Fluorescence and Electrochemiluminescence Emission

Peng Xu, Ningwen Sun, Xuan Thang Cao, Hui Xie, Yulan Zuo, H. Jia, Jinjin Ding, Qiang Huang, Jinling Zhang

2025Organic Letters6 citationsDOI

Abstract

Using dehydrobenzoannulene as an acceptor, two curved π-conjugated electron donor-acceptor architectures were concisely synthesized, and an unexpected deshielding effect was observed in the annulene fragment. Anomalously, the π-extended homologue exhibited blue-shifted fluorescence. Intriguingly, stunning and stable electrochemiluminescence emissions were first discovered in nonaromatic annulene derivatives. Finally, based on those electrochemiluminescence properties, a highly efficient sensor for detecting dopamine was constructed. This work provides new insights into molecular carbons and promotes the development of sensing in biological analysis.

Topics & Concepts

ChemistryElectrochemiluminescenceConjugated systemFluorescencePhotochemistryElectron acceptorAcceptorElectronNanotechnologyPhysical chemistryOrganic chemistryPhysicsOpticsMaterials scienceElectrodePolymerQuantum mechanicsPorphyrin and Phthalocyanine ChemistrySynthesis and Properties of Aromatic CompoundsSurface Chemistry and Catalysis