Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties
A series of α- and β-ethynyl-substituted BODIPY derivatives (3a, 4a, 5a, 5b, 6a, 6b) were synthesized by gold(I)-catalyzed direct C–H alkynylation reactions of dipyrromethane and BODIPY, respectively, with ethynylbenziodoxolone (EBX) in a regioselective manner. Depending on the position of the ethyn...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2020-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.16.53 |
| _version_ | 1818615768115314688 |
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| author | Takahide Shimada Shigeki Mori Masatoshi Ishida Hiroyuki Furuta |
| author_facet | Takahide Shimada Shigeki Mori Masatoshi Ishida Hiroyuki Furuta |
| author_sort | Takahide Shimada |
| collection | DOAJ |
| description | A series of α- and β-ethynyl-substituted BODIPY derivatives (3a, 4a, 5a, 5b, 6a, 6b) were synthesized by gold(I)-catalyzed direct C–H alkynylation reactions of dipyrromethane and BODIPY, respectively, with ethynylbenziodoxolone (EBX) in a regioselective manner. Depending on the position of the ethynyl substituent in the BODIPY skeleton, the photophysical properties of the resulting α- and β-substituted BODIPYs are notably altered. The lowest S0–S1 transition absorbance and fluorescence bands are both bathochromically shifted as the number of substituents increases, while the emission quantum yields of the β-ethynylated derivatives are significantly lower than those of α-ethynylated ones. The current method should be useful for fine-tuning of the photophysical properties of BODIPY dyes as well as for constructing BODIPY-based building cores for functional π-materials. |
| first_indexed | 2024-12-16T16:39:09Z |
| format | Article |
| id | doaj.art-855a0e3c6e894cfa82d93d09f6878a10 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T16:39:09Z |
| publishDate | 2020-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-855a0e3c6e894cfa82d93d09f6878a102022-12-21T22:24:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-04-0116158759510.3762/bjoc.16.531860-5397-16-53Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical propertiesTakahide Shimada0Shigeki Mori1Masatoshi Ishida2Hiroyuki Furuta3Department of Chemistry and Biochemistry, Graduate School of Engineering, and Center for Molecular Systems, Kyushu University, Fukuoka 819-0395, JapanAdvanced Research Support Center (ADRES), Ehime University, Matsuyama 790-8577, JapanDepartment of Chemistry and Biochemistry, Graduate School of Engineering, and Center for Molecular Systems, Kyushu University, Fukuoka 819-0395, JapanDepartment of Chemistry and Biochemistry, Graduate School of Engineering, and Center for Molecular Systems, Kyushu University, Fukuoka 819-0395, JapanA series of α- and β-ethynyl-substituted BODIPY derivatives (3a, 4a, 5a, 5b, 6a, 6b) were synthesized by gold(I)-catalyzed direct C–H alkynylation reactions of dipyrromethane and BODIPY, respectively, with ethynylbenziodoxolone (EBX) in a regioselective manner. Depending on the position of the ethynyl substituent in the BODIPY skeleton, the photophysical properties of the resulting α- and β-substituted BODIPYs are notably altered. The lowest S0–S1 transition absorbance and fluorescence bands are both bathochromically shifted as the number of substituents increases, while the emission quantum yields of the β-ethynylated derivatives are significantly lower than those of α-ethynylated ones. The current method should be useful for fine-tuning of the photophysical properties of BODIPY dyes as well as for constructing BODIPY-based building cores for functional π-materials.https://doi.org/10.3762/bjoc.16.53alkynylationbodipydirect c–h functionalizationgold(i) |
| spellingShingle | Takahide Shimada Shigeki Mori Masatoshi Ishida Hiroyuki Furuta Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties Beilstein Journal of Organic Chemistry alkynylation bodipy direct c–h functionalization gold(i) |
| title | Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties |
| title_full | Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties |
| title_fullStr | Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties |
| title_full_unstemmed | Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties |
| title_short | Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties |
| title_sort | regioselectively α and β alkynylated bodipy dyes via gold i catalyzed direct c h functionalization and their photophysical properties |
| topic | alkynylation bodipy direct c–h functionalization gold(i) |
| url | https://doi.org/10.3762/bjoc.16.53 |
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