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Control of the Emission Behaviors of Trifunctional o ‐Carborane Dyes
Author(s) -
Tominaga Masato,
Naito Hirofumi,
Morisaki Yasuhiro,
Chujo Yoshiki
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300280
Subject(s) - phenanthrene , bodipy , chemistry , carborane , intramolecular force , photochemistry , moiety , quenching (fluorescence) , organic chemistry , fluorescence , physics , quantum mechanics
Abstract A series of organic dyes were synthesized that contain an o ‐carborane unit in combination with phenanthrene, tolane, and BODIPY moieties. In solution, compound 7 a , which has phenanthrene and tolane units, does not emit as a result of an intramolecular charge transfer (ICT) from the emitters to the C1C2 bond of the o ‐carborane cage, whereas, in the aggregate and solid state, 7 a emits intense green light through aggregation‐induced emission (AIE). In solution, compound 7 b , which has phenanthrene, tolane, and BODIPY units, emits green light from the BODIPY moiety, whereas, in both the aggregate and solid state, it does not emit as a result of the energy transfer from the phenanthrene and tolanes to the neighboring BODIPY units and the successive aggregation‐caused quenching (ACQ) mechanism. This work shows that the emission behaviors, the ICT, AIE, energy transfer, and ACQ, of these dyes can be controlled by the substituents at the o ‐carborane core.