Iodization-enhanced fluorescence and circularly polarized luminescence for dual-readout probe design

Circularly polarized luminescence (CPL) is a preferential emission from chiral systems. Introducing CPL to traditional small fluorescence probes will greatly enhance selectivity and sensitivity due to avoiding the background fluorescence. Small-molecule probes are practically useful for bioimaging a...

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Bibliographic Details
Published in:Sensors and actuators. B, Chemical Chemical, 2021-11, Vol.347, p.130610, Article 130610
Main Authors: Gong, Jun, Huang, Ruishan, Wang, Chunfei, Zhao, Zujin, Tang, Ben Zhong, Zhang, Xuanjun
Format: Article
Language:English
Subjects:
Binaphthol
BODIPY
Chiral dynamics
Circular polarization
Circularly polarized luminescence
Fluorescent indicators
Iodization
Luminescence
Medical imaging
Optical properties
Perturbation
Selectivity
Sensitivity enhancement
Thiols
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Summary:Circularly polarized luminescence (CPL) is a preferential emission from chiral systems. Introducing CPL to traditional small fluorescence probes will greatly enhance selectivity and sensitivity due to avoiding the background fluorescence. Small-molecule probes are practically useful for bioimaging and sensing but always suffer from weak CPL properties. To optimize chiral perturbation, the study of structure-CPL correlation is an urgent necessity. Here, we investigated the influence of 3, 3′-substituent of BINOL on optical properties and found that iodization could significantly enhance the fluorescence quantum yield (ΦF) and dissymmetry factor (|glum|). Based on this finding, we presented a strategy to design dual-readout probes emiting both robust total fluorescence and CPL upon activation. As an application example, we first designed a pair of thiols probes, R/S-P1, with the fluorescence readout showing good linear response to cysteine, and CPL signal displaying significant enhancement with |glum| from undetectable value to 0.7 × 10−3. [Display omitted] •The iodization of BINOL enhanced 5-fold of the CPL brightness.•R/S-P1 exhibits a remarkable fluorescence enhancement towards cysteine.•The probe is ER-located and applied in living cells for sensing endogenous cysteine.•R-P1 displays distinct “off-on” CPL signal towards cysteine with |glum| value increasing to 0.7 × 10−3.
ISSN:0925-4005
1873-3077
DOI:10.1016/j.snb.2021.130610