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Phenothiazine Based Donor–Acceptor Compounds with Solid-State Emission in the Yellow to NIR Region and Their Highly Selective and Sensitive Detection of Cyanide Ion in ppb Level
Elumalai Ramachandran, Somasundaram Anbu Anjugam Vandarkuzhali,
Published in Wiley-VCH Verlag
2018
PMID: 29737000
Volume: 24
   
Issue: 43
Pages: 11042 - 11050
Abstract
Four new novel donor–acceptor (A-π-D-A, A-D-π-D-A) compounds (1 a, 1 b, 2 a and 2 b) based on ethylenedioxythiophene (EDOT) and phenothiazine (PTz) have been rationally designed and synthesized towards solid state emission ranging from yellow to near infrared (NIR). The compounds 1 b and 2 b, in thin film form, showed an emission maximum at 713 nm and 696 nm, respectively, with the corresponding absolute solid-state quantum yield of 3.3 % and 9.0 %. The fluorophores showed high emission in the doped state as well when dispersed in polystyrene (PS) matrix with emission maximum ranging from 536 nm to 648 nm with quantum yield in the range 12.4 %–64.4 %. The presence of dicyanovinyl (DCV) group in both the fluorophores was exploited towards cyanide sensing in DMSO leading to turn-on fluorescence emission with high selectivity and sensitivity for cyanide ion with a detection limit of as low as 0.32 μm (8 ppb) for 1 b and 0.57 μm (14 ppb) for 2 b. DFT and TTDFT calculations suggested that the addition of cyanide ion prevented the intramolecular charge transfer (ICT) from the donor (PTz or EDOT) to acceptor (DCV), thereby turning the fluorescence “On”. Using fluorescent spectral and color switching, we have explored logic gates with single and two input signal amplification by applying chemical and light inputs in the form of CN− ion and UV. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
About the journal
JournalData powered by TypesetChemistry - A European Journal
PublisherData powered by TypesetWiley-VCH Verlag
ISSN09476539
Open AccessNo
Concepts (23)
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    Charge transfer
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    Computer circuits
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    Cyanides
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    Doping (additives)
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    Fluorescence
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    Fluorophores
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    Infrared devices
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    Insecticides
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    Ions
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    Logic gates
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    Organic polymers
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    Quantum yield
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    Sensors
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    SOLID-STATE SENSORS
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    DONOR-ACCEPTOR COMPOUNDS
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    DONOR-ACCEPTOR SYSTEM
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    ETHYLENEDIOXYTHIOPHENES
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    Fluorescence emission
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    Intramolecular charge transfers
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    PHENOTHIAZINE
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    SIGNAL AMPLIFICATIONS
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    Solid state emission
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    Quantum theory