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Synthesis, Structure, and Properties of Near‐Infrared [ b ]Phenanthrene‐Fused BF 2 Azadipyrromethenes
Author(s) -
Cui Jiuen,
Sheng Wanle,
Wu Qinghua,
Yu Changjiang,
Hao Erhong,
BobadovaParvanova Petia,
Storer Marie,
Asiri Abdullah M.,
Marwani Hadi M.,
Jiao Lijuan
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700876
Subject(s) - bathochromic shift , phenanthrene , intramolecular force , photochemistry , annulation , chemistry , cyclic voltammetry , homo/lumo , tandem , absorption (acoustics) , ring (chemistry) , palladium , absorption spectroscopy , catalysis , materials science , organic chemistry , electrochemistry , molecule , fluorescence , physics , electrode , quantum mechanics , composite material
A new class of phenanthrene‐fused BF 2 azadipyrromethene (azaBODIPY) dyes have been synthesized through a tandem Suzuki reaction and oxidative ring‐fusion reaction, or a palladium‐catalyzed intramolecular C−H activation reaction. These phenanthrene‐fused azaBODIPY dyes are highly photostable and display markedly redshifted absorption (up to λ =771 nm) and emission bands ( λ ≈800 nm) in the near‐infrared region. DFT calculations and cyclic voltammetry studies indicate that, upon annulation, more pronounced stabilization of the LUMO is the origin of the bathochromic shift of the absorption and high photostability.