Metal-Free Catalytic Formation of a Donor-Acceptor-Donor Molecule and Its Lewis Acid-Adduct Singlet Diradical with High-Efficient NIR-II Photothermal Conversion
© 2024 Wiley‐VCH GmbH..
We have synthesized a quinone-incorporated bistriarylamine donor-acceptor-donor (D-A-D) semiconductor 1 by B(C6F5)3 (BCF) catalyzed C-H/C-H cross coupling via radical ion pair intermediates. Coordination of Lewis acids BCF and Al(ORF)3 (RF=C(CF3)3) to the semiconductor 1 afforded diradical zwitterions 2 and 3 by integer electron transfer. Upon binding to Lewis acids, the LUMO energy of 1 is significantly lowered and the band gap of the semiconductor is significantly narrowed from 1.93 eV (1) to 1.01 eV (2) and 1.06 eV (3). 2 and 3 are rare near-infrared (NIR) diradical dyes with broad absorption both centered around 1500 nm. By introducing a photo BCF generator, 2 can be generated by light-dependent control. Furthermore, the integer electron transfer process can also be reversibly regulated via the addition of CH3CN. In addition, the temperature of 2 sharply increased and reached as high as 110 °C in 10 s upon the irradiation of near-infrared-II (NIR-II) laser (1064 nm, 0.7 W cm-2), exhibiting a fast response to laser. It displays excellent photothermal stability with a photothermal (PT) conversion efficiency of 62.26 % and high-quality PT imaging.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:63 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 63(2024), 19 vom: 06. Apr., Seite e202400913 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Kong, Shanshan [VerfasserIn] |
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| Links: |
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| Themen: |
Integer electron transfer |
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| Anmerkungen: |
Date Revised 25.04.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202400913 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM369317734 |
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| 245 | 1 | 0 | |a Metal-Free Catalytic Formation of a Donor-Acceptor-Donor Molecule and Its Lewis Acid-Adduct Singlet Diradical with High-Efficient NIR-II Photothermal Conversion |
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2024 Wiley‐VCH GmbH. | ||
| 520 | |a We have synthesized a quinone-incorporated bistriarylamine donor-acceptor-donor (D-A-D) semiconductor 1 by B(C6F5)3 (BCF) catalyzed C-H/C-H cross coupling via radical ion pair intermediates. Coordination of Lewis acids BCF and Al(ORF)3 (RF=C(CF3)3) to the semiconductor 1 afforded diradical zwitterions 2 and 3 by integer electron transfer. Upon binding to Lewis acids, the LUMO energy of 1 is significantly lowered and the band gap of the semiconductor is significantly narrowed from 1.93 eV (1) to 1.01 eV (2) and 1.06 eV (3). 2 and 3 are rare near-infrared (NIR) diradical dyes with broad absorption both centered around 1500 nm. By introducing a photo BCF generator, 2 can be generated by light-dependent control. Furthermore, the integer electron transfer process can also be reversibly regulated via the addition of CH3CN. In addition, the temperature of 2 sharply increased and reached as high as 110 °C in 10 s upon the irradiation of near-infrared-II (NIR-II) laser (1064 nm, 0.7 W cm-2), exhibiting a fast response to laser. It displays excellent photothermal stability with a photothermal (PT) conversion efficiency of 62.26 % and high-quality PT imaging | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Integer electron transfer | |
| 650 | 4 | |a Lewis acid | |
| 650 | 4 | |a Metal-free catalysis | |
| 650 | 4 | |a NIR-II photothermal conversion | |
| 650 | 4 | |a Semiconductor | |
| 700 | 1 | |a Yang, Liming |e verfasserin |4 aut | |
| 700 | 1 | |a Sun, Quanchun |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Tao |e verfasserin |4 aut | |
| 700 | 1 | |a Pei, Runbo |e verfasserin |4 aut | |
| 700 | 1 | |a Zhao, Yue |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Wenqing |e verfasserin |4 aut | |
| 700 | 1 | |a Zhao, Yu |e verfasserin |4 aut | |
| 700 | 1 | |a Cui, Haiyan |e verfasserin |4 aut | |
| 700 | 1 | |a Gu, Xinggui |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Xinping |e verfasserin |4 aut | |
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