Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers
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 b...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-10-01
|
| Series: | International Journal of Molecular Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-0067/21/21/8041 |
| _version_ | 1797549532166225920 |
|---|---|
| author | Songlin Xue Daiki Kuzuhara Naoki Aratani Hiroko Yamada |
| author_facet | Songlin Xue Daiki Kuzuhara Naoki Aratani Hiroko Yamada |
| author_sort | Songlin Xue |
| collection | DOAJ |
| description | 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 3BF<sub>2</sub>-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. |
| first_indexed | 2024-03-10T15:15:56Z |
| format | Article |
| id | doaj.art-87890c91db254ddc89993b6e59149d9d |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T15:15:56Z |
| publishDate | 2020-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-87890c91db254ddc89993b6e59149d9d2023-11-20T18:54:54ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672020-10-012121804110.3390/ijms21218041Vinylene-Bridged Cyclic Dipyrrin and BODIPY TrimersSonglin Xue0Daiki Kuzuhara1Naoki Aratani2Hiroko Yamada3School of Chemistry and Chemical Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang 212013, ChinaFaculty of Science and Engineering, Iwate University, 4-3-5 Ueda, Morioka, Iwate 020-8551, JapanDivision of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama-cho, Ikoma, Nara 630-0192, JapanDivision of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama-cho, Ikoma, Nara 630-0192, JapanVinylene-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 3BF<sub>2</sub>-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.https://www.mdpi.com/1422-0067/21/21/8041expanded porphyrinboron complexmolecular configuration |
| spellingShingle | Songlin Xue Daiki Kuzuhara Naoki Aratani Hiroko Yamada Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers International Journal of Molecular Sciences expanded porphyrin boron complex molecular configuration |
| title | Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers |
| title_full | Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers |
| title_fullStr | Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers |
| title_full_unstemmed | Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers |
| title_short | Vinylene-Bridged Cyclic Dipyrrin and BODIPY Trimers |
| title_sort | vinylene bridged cyclic dipyrrin and bodipy trimers |
| topic | expanded porphyrin boron complex molecular configuration |
| url | https://www.mdpi.com/1422-0067/21/21/8041 |
| work_keys_str_mv | AT songlinxue vinylenebridgedcyclicdipyrrinandbodipytrimers AT daikikuzuhara vinylenebridgedcyclicdipyrrinandbodipytrimers AT naokiaratani vinylenebridgedcyclicdipyrrinandbodipytrimers AT hirokoyamada vinylenebridgedcyclicdipyrrinandbodipytrimers |