Synthesis, Crystal Structure, and Photophysical Properties of Bromothiophene-Functionalized BF2-Curcuminoid as a Versatile Building Block
Haixia Kang
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorQilian Wang
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorXingrui Gao
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorYongliang Feng
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorHemin Xu
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorJinzhao Song
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorJingfang Han
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorLiujing Gao
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorCorresponding Author
Ziyong Li
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
E-mail: [email protected]
Search for more papers by this authorHaixia Kang
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorQilian Wang
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorXingrui Gao
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorYongliang Feng
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorHemin Xu
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorJinzhao Song
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorJingfang Han
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorLiujing Gao
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
Search for more papers by this authorCorresponding Author
Ziyong Li
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, 471934 P. R. China
E-mail: [email protected]
Search for more papers by this authorAbstract
A novel bromothiophene-functionalized BF2-curcuminoid (BTC-BF2) is synthesized by Knoevenagel condensation reaction. The structure of BTC-BF2 is determined by 1H-nuclear magnetic resonance (1H NMR), 13C-nuclear magnetic resonance (13C NMR), and high-resolution mass spectrometry (HRMS). Moreover, a nearly coplanar single crystal structure is successfully obtained and form a mesh structure through intermolecular multiple C─H···F hydrogen bond interactions. As expected, as-prepared BTC-BF2 exhibits solvent-dependent photophysical properties in solvents with different polarity and an intense red solid-state fluorescence. Density functional theory calculations further verify the relationships between its intrinsic electronic features and the photophysical properties. For its potential application aspect, BTC-BF2 shows a certain ability to generate singlet oxygen under irradiation with 530 nm green light. Moreover, BTC-BF2 can be utilized as versatile building block to construct novel far-red or NIR BF2-curcuminoid complexes for widely biological applications.
Conflict of Interest
The authors declare no conflict of interest
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
Supporting Information
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