Hybrid Planar–Twisted Chair‐Shaped Indoline Donor Enabling Bright Molecular and Aggregated State Near‐Infrared Emission
Abstract
Abstract Organic near‐infrared (NIR) fluorophores with donor–acceptor (D–A) architectures have emerged as a preeminent paradigm in optoelectronic engineering and biomedical applications. However, conventional D–A NIR emitters often suffer from aggregation‐induced quenching or weak absorption owing to the use of planar (e.g., carbazole) or highly twisted (e.g., triphenylamine) donor units, which impairs their versatile utility in molecular and aggregated states. Herein, we proposed a unique chair‐shaped indoline donor ( c ID) with a hybrid planar–twisted conformation, which affords bright various states (solution, solid, microspheres, nanoparticles, and films) NIR emission spanning 650–1200 nm, with tails extending to 1600 nm. The c ID donor promotes electron localization, imparting higher oscillator strength and a smaller HOMO–LUMO energy gap to the designed NIR fluorophores, which together enhance light‐harvesting capacity and induce red‐shifted emission. Meanwhile, the sterically hindered nonconjugated group in c ID effectively restricts low frequency vibration‐induced non‐radiative decay, as evidenced by the reduced reorganization energy and Huang–Rhys factor in both isolated and crystalline phase. Through structurally π‐conjugation extension, these NIR fluorophores exhibit robust various‐state NIR‐I (photoluminescence quantum yields up to 67.8% and brightness up to 15668 M −1 cm −1 ) and NIR‐II emission, which allows diverse advanced applications in porous ceramic damage detection, stimulated emission depletion (STED) microscopy, and NIR‐II vascular imaging, thereby positioning c ID as a versatile toolkit to create a novel NIR dye library for biomedical and optoelectronic field.
Article Details
Authors (14)
Qiqi Xu
Ying Wang
Yiyan Guan
Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM) Nanjing Tech University (Nanjing Tech) Nanjing China
Chenggong Ma
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Shanghai Key Laboratory of Functional Materials Chemistry, Feringa Nobel Prize Scientist Joint Research Center, Institute of Fine Chemicals, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering
Guofeng Yi
State Key Laboratory of Green Chemical Engineering and Industrial Catalysis Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Shanghai Key Laboratory of Functional Materials Chemistry Feringa Nobel Prize Scientist Joint Research Center Institute of Fine Chemicals Frontiers Science Center For Materiobiology and Dynamic Chemistry School of Chemistry and Molecular Engineering East China University of Science and...
Xinyun Du
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Shanghai Key Laboratory of Functional Materials Chemistry Feringa Nobel Prize Scientist Joint Research Center Institute of Fine Chemicals Frontiers Science Center for Materiobiology and Dynamic Chemistry School of Chemistry and Molecular Engineering East China University of Science and Technology Shanghai 200237 China
Haile Bin
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Shanghai Key Laboratory of Functional Materials Chemistry Feringa Nobel Prize Scientist Joint Research Center Institute of Fine Chemicals Frontiers Science Center for Materiobiology and Dynamic Chemistry School of Chemistry and Molecular Engineering East China University of Science and Technology Shanghai 200237 China
Wentao Shen
State Key Laboratory for Animal Disease Control and Prevention, College of Veterinary Medicine, Lanzhou University, Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences
Cheng‐Yun Wang
State Key Laboratory of Green Chemical Engineering and Industrial Catalysis Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Shanghai Key Laboratory of Functional Materials Chemistry Feringa Nobel Prize Scientist Joint Research Center Institute of Fine Chemicals Frontiers Science Center For Materiobiology and Dynamic Chemistry School of Chemistry and Molecular Engineering East China University of Science and...
Yongzhen Wu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Shanghai Key Laboratory of Functional Materials Chemistry, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering
Huili Ma
State Key Laboratory of Flexible Electronics (LoFE) & Institute of Advanced Materials (IAM), School of Flexible Electronics (Future Technologies)
Fei Tong
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
Wei‐Hong Zhu
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Shanghai Key Laboratory of Functional Materials Chemistry Feringa Nobel Prize Scientist Joint Research Center Institute of Fine Chemicals Frontiers Science Center For Materiobiology and Dynamic Chemistry School of Chemistry and Molecular Engineering East China University of Science and Technology Shanghai China
Weijun Zhao
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Shanghai Key Laboratory of Functional Materials Chemistry, Feringa Nobel Prize Scientist Joint Research Center, Institute of Fine Chemicals, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering