Metal-Free Catalytic Formation of a Donor-Acceptor-Donor Molecule and Its Lewis Acid-Adduct Singlet Diradical with High-Efficient NIR-II Photothermal Conversion.
Angew Chem Int Ed Engl
; 63(19): e202400913, 2024 May 06.
Article
en En
| MEDLINE
| ID: mdl-38441914
ABSTRACT
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 1.93â
eV (1) to 1.01â
eV (2) and 1.06â
eV (3). 2 and 3 are rare near-infrared (NIR) diradical dyes with broad absorption both centered around 1500â
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 10â
s upon the irradiation of near-infrared-II (NIR-II) laser (1064â
nm, 0.7â
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.
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MEDLINE
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En
Revista:
Angew Chem Int Ed Engl
Año:
2024
Tipo del documento:
Article
País de afiliación:
China