Design of twisted NIR BOPYIN with highly fluorescent intensity for monitoring viscosity

被引:6
作者
Yuan, Xiaohui [1 ]
Hu, Yanjun [2 ]
Zheng, Kaibo [1 ,3 ]
Liu, Debao [1 ]
Su, Peng [1 ]
Hu, Cong [1 ]
Yan, Jiaying [1 ,3 ]
Zhang, Nuonuo [1 ,3 ]
机构
[1] China Three Gorges Univ, Coll Mat & Chem Engn, Key Lab Inorgan Nonmetall Crystalline & Energy Co, Yichang 443002, Hubei, Peoples R China
[2] Shandong Chenming Paper Holdings Ltd, Shouguang 262700, Shandong, Peoples R China
[3] Hubei Three Gorges Lab, Yichang 443007, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
BOPYIN; NIR fluorescent dye; Viscosity; Molecular rotor; Motion-induced change in emission; MITOCHONDRIAL VISCOSITY; LYSOSOMAL VISCOSITY; ALZHEIMERS-DISEASE; LIVING CELLS; PROBE; 2-PHOTON; COUMARIN; ROTOR;
D O I
10.1016/j.molliq.2022.118493
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A set of BOPYIN-based molecular rotors have been systematically synthesized and investigated to study the relationship between intramolecular motions and viscosity sensitivity. YD6 possesses NIR emission at 723 nm, high quantum yield (19-48%) and large Stokes shift (2620-5144 cm(-1)) due to the twisted structure via the single crystal structure. YD1-3,5,6 show high viscosity response with dye-dependent constants ranging from 0.21 to 0.39. Through experimental and computational studies, the different substituent strongly influences the viscosity sensitivity, likely resulting from inherent rotational energy barriers between the twisted configurations. These findings enable rational structure modifications of BOPYIN molecular rotors for highly effective viscosity detection and recognition. (C) 2022 Elsevier B.V. All rights reserved.
引用
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页数:9
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共 57 条
  • [1] Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD-DFT, and NLO Properties
    Bhalekar, Sulochana B.
    Kothavale, Shantaram
    Sekar, Nagaiyan
    [J]. CHEMISTRYSELECT, 2019, 4 (43): : 12512 - 12523
  • [2] REMARKS ON THE USE OF THE APPARENT SURFACE-CHARGES (ASC) METHODS IN SOLVATION PROBLEMS - ITERATIVE VERSUS MATRIX-INVERSION PROCEDURES AND THE RENORMALIZATION OF THE APPARENT CHARGES
    CAMMI, R
    TOMASI, J
    [J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1995, 16 (12) : 1449 - 1458
  • [3] Sensing and imaging of mitochondrial viscosity in living cells using a red fluorescent probe with a long lifetime
    Chen, Bochao
    Li, Chengde
    Zhang, Jie
    Kan, Jianfei
    Jiang, Tiantian
    Zhou, Jin
    Ma, Huimin
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (51) : 7410 - 7413
  • [4] A deep-red emission fluorescent probe with long wavelength absorption for viscosity detection and live cell imaging
    Chen, Li
    Feng, Yangzhen
    Dang, Yecheng
    Zhong, Cheng
    Chen, Dugang
    [J]. ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2020, 412 (28) : 7819 - 7826
  • [5] Visualization of ONOO- and Viscosity in Drug-Induced Hepatotoxicity with Different Fluorescence Signals by a Sensitive Fluorescent Probe
    Deng, Yingzhen
    Feng, Guoqiang
    [J]. ANALYTICAL CHEMISTRY, 2020, 92 (21) : 14667 - 14675
  • [6] SELF-CONSISTENT MOLECULAR-ORBITAL METHODS .9. EXTENDED GAUSSIAN-TYPE BASIS FOR MOLECULAR-ORBITAL STUDIES OF ORGANIC MOLECULES
    DITCHFIELD, R
    HEHRE, WJ
    POPLE, JA
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1971, 54 (02) : 724 - +
  • [7] Design of Activatable NIR-II Molecular Probe for In Vivo Elucidation of Disease-Related Viscosity Variations
    Dou, Kun
    Huang, Weijing
    Xiang, Yunhui
    Li, Songjiao
    Liu, Zhihong
    [J]. ANALYTICAL CHEMISTRY, 2020, 92 (06) : 4177 - 4181
  • [8] A near-infrared fluorescent probe with large Stokes shift for visualizing and monitoring mitochondrial viscosity in live cells and inflammatory tissues
    Fan, Lixue
    Pan, Yanping
    Li, Weiqing
    Xu, Yue
    Duan, Yishan
    Li, Ruixi
    Lv, Yanqing
    Chen, Haiyan
    Yuan, Zhenwei
    [J]. ANALYTICA CHIMICA ACTA, 2021, 1149
  • [9] Dual-detection of mitochondrial viscosity and SO2 derivatives with two cross-talk-free emissions employing a single two-photon fluorescent probe
    Fang, Guoshun
    Yang, Xiuli
    Wang, Wenjuan
    Feng, Yan
    Zhang, Wan
    Huang, Yinliang
    Sun, Chuan
    Chen, Man
    Meng, Xiangming
    [J]. SENSORS AND ACTUATORS B-CHEMICAL, 2019, 297
  • [10] A highly sensitive red-emitting probe for the detection of viscosity changes in living cells, zebrafish, and human blood samples
    Fu, Manlin
    Shen, Wei
    Chen, Yajun
    Yi, Wenjun
    Cai, Chunhui
    Zhu, Liquan
    Zhu, Qing
    [J]. JOURNAL OF MATERIALS CHEMISTRY B, 2020, 8 (06) : 1310 - 1315