Metal‐Free Catalytic Formation of a Donor‐Acceptor‐Donor Molecule and Its Lewis Acid‐Adduct Singlet Diradical with High‐Efficient NIR‐II Photothermal Conversion

Author:

Kong Shanshan1,Yang Liming2,Sun Quanchun1,Wang Tao1,Pei Runbo1,Zhao Yue1,Wang Wenqing3,Zhao Yu1,Cui Haiyan4ORCID,Gu Xinggui2ORCID,Wang Xinping15ORCID

Affiliation:

1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures Nanjing University Nanjing 210023 China

2. Beijing Advanced Innovation Center for Soft Matter Science and Engineering, College of Materials Science and Engineering Beijing University of Chemical Technology Beijing 100029 China

3. College of Chemistry and Materials Science, Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Moleculer-Based Materials Anhui Normal University Wuhu 241002 China

4. Jiangsu Key Laboratory of Pesticide Science, College of Sciences Nanjing Agricultural University Nanjing 210095 China

5. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Science Shanghai 200032 China

Abstract

AbstractWe 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.

Funder

National Natural Science Foundation of China

Publisher

Wiley

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1. Crystalline Boron‐Centered Analogues of Müller's Hydrocarbon;Chinese Journal of Chemistry;2024-06-16

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