Condensed Osmaquinolines with NIR-II Absorption Synthesized by Aryl C−H Annulation and Aromatization

Cui，Fei Hu1; Li，Qian1; Gao，Le Han1; Ruan，Kaidong1; Ma，Kexin1; Chen，Siyuan1; Lu，Zhengyu2; Fei，Jiawei1; Lin，Yu Mei1; Xia，Haiping1,2

2022

10.1002/anie.202211734

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Impact Factor & Quartile

1433-7851

1521-3773

The structural design and tuning of properties of metallaaromatics are crucial in materials and energy science. Herein, we describe the rapid synthesis of tetracyclic metallaaromatics containing quinoline and pentalene motifs fused by a metal-bridged fragment. These unique compounds display remarkably broad absorption, enabling for the first time the absorption of metallaaromatics to reach the second near-infrared (NIR-II) bio-window. The formation of osmaquinoline unit involves an unconventional C(sp)−C(sp) coupling promoted by AgBF to achieve [3+3] cycloaddition. The introduction of cyclic d-p conjugation and extension of the aromatic π-framework can effectively shrink the HOMO–LUMO gap, thus broadening the absorption window. The considerable photothermal conversion efficiency (PCE) in both the NIR-I and NIR-II windows, the high photothermal stability and the excellent electrochemical behavior suggest many potential applications of these condensed metallaquinolines.

Anthranil dπ-pπ Conjugation Metallaaromatics NIR-II Absorption [3+3] Annulation

SCI

English

NI Journal Papers

Corresponding

Natural Science Foundation of China["22071206","92156021","21931002"] ; Natural Science Foundation of Fujian Province of China[2020J01025] ; Shenzhen Science and Technology Innovation Committee[JCYJ20200109140812302] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Multidisciplinary

WOS:000871723500001

WILEY-V C H VERLAG GMBH

CHEMISTRY

2-s2.0-85141208439

Scopus

1.College of Chemistry and Chemical Engineering,Xiamen University,Xiamen,361005,China
2.Shenzhen Grubbs Institute,Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China

Cui，Fei Hu,Li，Qian,Gao，Le Han,et al. Condensed Osmaquinolines with NIR-II Absorption Synthesized by Aryl C−H Annulation and Aromatization[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2022.

Cui，Fei Hu.,Li，Qian.,Gao，Le Han.,Ruan，Kaidong.,Ma，Kexin.,...&Xia，Haiping.(2022).Condensed Osmaquinolines with NIR-II Absorption Synthesized by Aryl C−H Annulation and Aromatization.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.

Cui，Fei Hu,et al."Condensed Osmaquinolines with NIR-II Absorption Synthesized by Aryl C−H Annulation and Aromatization".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022).