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Facile Route to Novel Diazaphosphinine‐Based Polycyclic Aromatic Hydrocarbons

Zi Yang, Can Li, Xingchen Liu, Xinyu Li, Na Yu, Yi Ren

2022Angewandte Chemie International Edition22 citationsDOI

Abstract

Doping main-group elements has become a unique strategy to fine-tune optoelectronic properties of organic π-conjugated molecules. Herein, we report the first example of diazaphosphinine based polycyclic hydrocarbons (DP-PAHs) via facile synthetic protocols. Synthesis of diazaphosphinine heterocycles harnesses mild and efficient P-N chemistry. The heterocycles readily undergo photocyclizations by using only oxidants. The photocyclization protocol is applicable to the heterocycles with various P-centers. We successfully extended the protocols in extended DP-PAHs with 13-fused aromatic rings. Further adjusting P-chemistry allows to efficiently fine-tune the singlet and triplet emission characteristics. More importantly, single-molecule white-light-emitting character was achieved via the balanced singlet and triplet emission of DP-PAH. Therefore, this work opens up new horizons in the area of organic π-conjugated materials.

Topics & Concepts

Conjugated systemMoleculeSinglet stateChemistrySinglet oxygenCombinatorial chemistryDopingPhotochemistryOrganic chemistryMaterials scienceOptoelectronicsPolymerPhysicsOxygenExcited stateNuclear physicsLuminescence and Fluorescent MaterialsOrganoboron and organosilicon chemistrySynthesis and Properties of Aromatic Compounds
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