Conformationally restricted aza-dipyrromethene boron difluorides (aza-BODIPYs) with high fluorescent quantum yields.
A simple approach to the highly fluorescent near-infrared aza-BODIPY dyes with higher fluorescence quantum yields (up to 0.81 in toluene) in comparison with their known analogues is presented. Our approach is based on the restricted rotations of the 1,7-phenyl groups to the mean plane of the aza-BODIPYs, which is achieved through the installation of bulky substituents on the 1,7-phenyl groups of aza-BODIPYs and results in a reduced nonradiative relaxation process in solution. The large torsion angles between the 1,7-phenyl groups and the aza-BODIPY core (ϕ1 and ϕ2 in these novel conformationally restricted aza-BODIPYs) were confirmed by X-ray diffraction studies.
The Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, 241000 (China). jiao421@mail.ahnu.edu.cn.
Lijuan
L
Jiao
Yayang
Y
Wu
Yin
Y
Ding
Sufan
S
Wang
Ping
P
Zhang
Changjiang
C
Yu
Yun
Y
Wei
Xiaolong
X
Mu
Erhong
E
Hao
D001372:Aza Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D011162:Porphobilinogen / Q000031:analogs & derivatives* / Q000737:chemistry; D011789:Quantum Theory; D012997:Solvents / Q000737:chemistry
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001372:Aza Compounds; D001896:Boron Compounds; D005456:Fluorescent Dyes; D012997:Solvents; C507544:dipyrromethene; D011162:Porphobilinogen; D005459:Fluorides
BODIPY; N ligands; dyes/pigments; fluorescence; heterocycles