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Article

Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers

1
School of Chemistry and Chemical Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang 212013, China
2
Faculty of Science and Engineering, Iwate University, 4-3-5 Ueda, Morioka, Iwate 020-8551, Japan
3
Division of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(21), 8041; https://doi.org/10.3390/ijms21218041
Received: 12 September 2020 / Revised: 21 October 2020 / Accepted: 22 October 2020 / Published: 28 October 2020
(This article belongs to the Special Issue Synthesis and Reactivity of Novel Aromatic Compounds)
Vinylene-bridged cyclic boron–difluoride complex of dipyrrin (BODIPY) trimers were successfully prepared from expanded dimethyl-vinylene bridged hexaphyrin(2.1.2.1.2.1) Me-Hex that has the structure of alternate dipyrrins and vinylene bridges. The hexaphyrin(2.1.2.1.2.1) Me-Hex can coordinate with boron ions to afford five kinds of cyclic BODIPYs given by step-by-step boron complexations. Crystal structures of all cyclic BODIPYs except for 3BF2-Me-Hex(b) formed non-planar structures. The theoretical calculation predicted that mono-/bis-boron cyclic BODIPYs show the intramolecular charge transfer (ICT) characteristics, whereas tri-boron cyclic BODIPYs have no ICT characteristics. Reflecting these electronic properties, tri-boron cyclic BODIPYs exhibit weak fluorescence in the red region, but mono-/bis-boron cyclic BODIPYs exhibit no emission. Vinylene bridged cyclic dipyrrin trimer Me-Hex is the novel porphyrinoid ligand allowed to control the boron coordination under different reaction conditions to form various boron complexes. View Full-Text
Keywords: expanded porphyrin; boron complex; molecular configuration expanded porphyrin; boron complex; molecular configuration
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MDPI and ACS Style

Xue, S.; Kuzuhara, D.; Aratani, N.; Yamada, H. Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers. Int. J. Mol. Sci. 2020, 21, 8041. https://doi.org/10.3390/ijms21218041

AMA Style

Xue S, Kuzuhara D, Aratani N, Yamada H. Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers. International Journal of Molecular Sciences. 2020; 21(21):8041. https://doi.org/10.3390/ijms21218041

Chicago/Turabian Style

Xue, Songlin, Daiki Kuzuhara, Naoki Aratani, and Hiroko Yamada. 2020. "Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers" International Journal of Molecular Sciences 21, no. 21: 8041. https://doi.org/10.3390/ijms21218041

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