Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety
An asymmetric aza-BODIPY analogue bearing quinoxaline moiety was synthesized via a titanium tetrachloride-mediated Schiff-base-forming reaction of 6,7-dimethyl-1,4-dihydroquinoxaline-2,3-dione and benzo[<i>d</i>]thiazol-2-amine. This novel aza-BODIPY analogue forms a complementary hydrog...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/24/7940 |
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| author | Ru Feng Zuoxu Chen Yue Wang Jianming Pan Soji Shimizu |
| author_facet | Ru Feng Zuoxu Chen Yue Wang Jianming Pan Soji Shimizu |
| author_sort | Ru Feng |
| collection | DOAJ |
| description | An asymmetric aza-BODIPY analogue bearing quinoxaline moiety was synthesized via a titanium tetrachloride-mediated Schiff-base-forming reaction of 6,7-dimethyl-1,4-dihydroquinoxaline-2,3-dione and benzo[<i>d</i>]thiazol-2-amine. This novel aza-BODIPY analogue forms a complementary hydrogen-bonded dimer due to the quinoxaline moiety in the crystal structure. It also shows intense absorption and fluorescence, with fluorescence quantum yields close to unity. The electrochemical measurements and the DFT calculations revealed the presence of the low-lying HOMO, which benefits their potential applications as an electron-transporting material. |
| first_indexed | 2024-03-08T20:30:51Z |
| format | Article |
| id | doaj.art-5e71eb6198bc4adb89ee9c30e2750f43 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-08T20:30:51Z |
| publishDate | 2023-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5e71eb6198bc4adb89ee9c30e2750f432023-12-22T14:27:08ZengMDPI AGMolecules1420-30492023-12-012824794010.3390/molecules28247940Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline MoietyRu Feng0Zuoxu Chen1Yue Wang2Jianming Pan3Soji Shimizu4School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, ChinaSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, ChinaSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, ChinaSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, ChinaDepartment of Applied Chemistry, Graduate School of Engineering, Kyushu University, Fukuoka 819-0395, JapanAn asymmetric aza-BODIPY analogue bearing quinoxaline moiety was synthesized via a titanium tetrachloride-mediated Schiff-base-forming reaction of 6,7-dimethyl-1,4-dihydroquinoxaline-2,3-dione and benzo[<i>d</i>]thiazol-2-amine. This novel aza-BODIPY analogue forms a complementary hydrogen-bonded dimer due to the quinoxaline moiety in the crystal structure. It also shows intense absorption and fluorescence, with fluorescence quantum yields close to unity. The electrochemical measurements and the DFT calculations revealed the presence of the low-lying HOMO, which benefits their potential applications as an electron-transporting material.https://www.mdpi.com/1420-3049/28/24/7940aza-BODIPYquinoxalinehydrogen bondingfluorescence |
| spellingShingle | Ru Feng Zuoxu Chen Yue Wang Jianming Pan Soji Shimizu Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety Molecules aza-BODIPY quinoxaline hydrogen bonding fluorescence |
| title | Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety |
| title_full | Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety |
| title_fullStr | Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety |
| title_full_unstemmed | Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety |
| title_short | Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety |
| title_sort | facile synthesis of asymmetric aza boron dipyrromethene analogues bearing quinoxaline moiety |
| topic | aza-BODIPY quinoxaline hydrogen bonding fluorescence |
| url | https://www.mdpi.com/1420-3049/28/24/7940 |
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