BAr2‐bridged Azafulvene Dimers with Tunable Energy Levels for Photostable Near‐infrared Dyes
BAr2‐bridged Azafulvene Dimers with Tunable Energy Levels for Photostable Near‐infrared Dyes
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用于光稳定近红外染料的具有可调能级的 BAr2 桥联氮杂富烯二聚体
DOI：
10.1002/chem.202300529
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发表时间：
2023
影响因子：
4.3
通讯作者：
Wakamiya Atsushi
中科院分区：
文献类型：
--
作者：
Tan Tiancheng;Nakamura Tomoya;Murdey Richard;Hu Shuaifeng;Truong Minh Anh;Wakamiya Atsushi
在近红外（NIR）区域具有强吸收的有机染料在医学应用中具有潜在的用途，例如肿瘤成像和光热治疗。在这项工作中，新的近红外染料结合BAr 2-桥氮杂富烯二聚体受体与二芳基氨基噻吩供体在供体-受体-供体配置合成。令人惊讶的是，发现在这些分子中，BAr 2-桥连的氮杂富烯受体采用5元环结构，而不是6元环结构。从电化学和光学测量上的染料化合物的HOMO和LUMO能级的芳基取代基的影响进行了评估。强吸电子氟化取代基（Ar= C6 F5，3，5-（CF 3）2C 6 H3）降低了HOMO能量，同时保持了小的HOMO-LUMO能隙，从而产生了有前途的NIR染料分子，其联合收割机以900 nm为中心的强吸收带和良好的光稳定性。
Organic dyes with strong absorption in the near‐infrared (NIR) region are potentially useful in medical applications, such as tumor imaging and photothermal therapy. In this work, new NIR dyes combining BAr2‐bridged azafulvene dimer acceptors with diarylaminothienyl donors in a donor–acceptor–donor configuration were synthesized. Surprisingly, it was found that in these molecules the BAr2‐bridged azafulvene acceptor adopts a 5‐membered, rather than 6‐membered ring structure. The influence of the aryl substituents on the HOMO and LUMO energy levels of the dye compounds was assessed from electrochemical and optical measurements. Strong electron‐withdrawing fluorinated substituents (Ar=C6F5, 3,5‐(CF3)2C6H3) lowered the HOMO energy while preserving the small HOMO–LUMO energy gap, resulting in promising NIR dye molecules that combine strong absorption bands centered around 900 nm with good photostability.