Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole‐porphyrin‐based near‐infrared dyes
Abstract Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole (BBT) has intrinsic diradical character and herein it is used to construct organic near‐infrared (NIR) dyes together with the aromatic porphyrin unit. Three BBT‐porphyrin hybrid dyes 1–3 with different linkage modes are synthesized by Pd‐catalyzed So...
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Wiley
2021-09-01
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| Series: | SmartMat |
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| Online Access: | https://doi.org/10.1002/smm2.1066 |
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doaj-a15b8fa1205a4c32bc09cd9c039f19ae2021-09-30T20:05:11ZengWileySmartMat2688-819X2021-09-012339840510.1002/smm2.1066Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole‐porphyrin‐based near‐infrared dyesYi Liu0Shaofei Wu1Tullimilli Y. Gopalakrishna2Jishan Wu3Department of Chemistry National University of Singapore Singapore SingaporeDepartment of Chemistry National University of Singapore Singapore SingaporeDepartment of Chemistry National University of Singapore Singapore SingaporeJoint School of National University of Singapore and Tianjin University International Campus of Tianjin University Fuzhou, Binhai New City ChinaAbstract Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole (BBT) has intrinsic diradical character and herein it is used to construct organic near‐infrared (NIR) dyes together with the aromatic porphyrin unit. Three BBT‐porphyrin hybrid dyes 1–3 with different linkage modes are synthesized by Pd‐catalyzed Sonogashira cross‐coupling between meso‐ethynylene porphyrin units and monobromo‐/dibromo‐ BBT, or through unexpected homocoupling between the BBT units. They all possess small open‐shell diradical character and display intense NIR absorption in the range of 800–1000 nm. They also exhibit amphoteric redox behavior. BBT‐based diradicaloids are thus good candidates for organic NIR dyes.https://doi.org/10.1002/smm2.1066benzo[1,2‐c;4,5‐c']bis[1,2,5]thiadiazolediradical characternear‐infrared dyeporphyrin |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Yi Liu Shaofei Wu Tullimilli Y. Gopalakrishna Jishan Wu |
| spellingShingle |
Yi Liu Shaofei Wu Tullimilli Y. Gopalakrishna Jishan Wu Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole‐porphyrin‐based near‐infrared dyes SmartMat benzo[1,2‐c;4,5‐c']bis[1,2,5]thiadiazole diradical character near‐infrared dye porphyrin |
| author_facet |
Yi Liu Shaofei Wu Tullimilli Y. Gopalakrishna Jishan Wu |
| author_sort |
Yi Liu |
| title |
Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole‐porphyrin‐based near‐infrared dyes |
| title_short |
Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole‐porphyrin‐based near‐infrared dyes |
| title_full |
Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole‐porphyrin‐based near‐infrared dyes |
| title_fullStr |
Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole‐porphyrin‐based near‐infrared dyes |
| title_full_unstemmed |
Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole‐porphyrin‐based near‐infrared dyes |
| title_sort |
benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole‐porphyrin‐based near‐infrared dyes |
| publisher |
Wiley |
| series |
SmartMat |
| issn |
2688-819X |
| publishDate |
2021-09-01 |
| description |
Abstract Benzo[1,2‐c;4,5‐cʹ]bis[1,2,5]thiadiazole (BBT) has intrinsic diradical character and herein it is used to construct organic near‐infrared (NIR) dyes together with the aromatic porphyrin unit. Three BBT‐porphyrin hybrid dyes 1–3 with different linkage modes are synthesized by Pd‐catalyzed Sonogashira cross‐coupling between meso‐ethynylene porphyrin units and monobromo‐/dibromo‐ BBT, or through unexpected homocoupling between the BBT units. They all possess small open‐shell diradical character and display intense NIR absorption in the range of 800–1000 nm. They also exhibit amphoteric redox behavior. BBT‐based diradicaloids are thus good candidates for organic NIR dyes. |
| topic |
benzo[1,2‐c;4,5‐c']bis[1,2,5]thiadiazole diradical character near‐infrared dye porphyrin |
| url |
https://doi.org/10.1002/smm2.1066 |
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