Thiazolidine-Based Fluorescent Chiral Ionic Liquids for Trace Copper(II) Ion Sensing

This study presents a comprehensive analysis of the synthesis and photophysical properties of thiazolidine-functionalized chiral ionic liquids (CILs) derived from L-cysteine. The synthesis involves a four-step route, encompassing N-protection, coupling reactions with bromoalcohols, and ionic liquid...

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Published inCompounds Vol. 3; no. 3; pp. 430 - 446
Main Authors Griebeler, Cassiana H., Bach, Mariana F., Silva, Henrique C., Rodembusch, Fabiano S., Coelho, Felipe L., Schneider, Paulo H.
Format Journal Article
LanguageEnglish
Published MDPI AG 01.09.2023
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Abstract This study presents a comprehensive analysis of the synthesis and photophysical properties of thiazolidine-functionalized chiral ionic liquids (CILs) derived from L-cysteine. The synthesis involves a four-step route, encompassing N-protection, coupling reactions with bromoalcohols, and ionic liquid formation. The optical properties of the compounds were evaluated using UV–Vis absorption and fluorescence emission spectroscopies, revealing distinct behavior for different heterocycles and counter-ions. Notably, the investigation reveals that thiazolidine-based CILs exhibit unconventional intrinsic luminescence characteristics. Building upon these photophysical properties, an interaction study was conducted between copper (II) and the CILs. The findings exhibit a robust linear relationship between the optical response and the concentration of the metal ion. Through the calculation of the Stern–Volmer quenching constant, it was determined that the 1:1 binding model is applicable. This research underscores the potential of UV–Vis absorption spectroscopy as a highly sensitive method for detecting metal ions. By elucidating the synthesis, photophysical behavior, and metal ion interaction of thiazolidine-based CILs, this study contributes valuable insights into the field of functionalized ionic liquids and their potential applications in various areas.
AbstractList This study presents a comprehensive analysis of the synthesis and photophysical properties of thiazolidine-functionalized chiral ionic liquids (CILs) derived from L-cysteine. The synthesis involves a four-step route, encompassing N-protection, coupling reactions with bromoalcohols, and ionic liquid formation. The optical properties of the compounds were evaluated using UV–Vis absorption and fluorescence emission spectroscopies, revealing distinct behavior for different heterocycles and counter-ions. Notably, the investigation reveals that thiazolidine-based CILs exhibit unconventional intrinsic luminescence characteristics. Building upon these photophysical properties, an interaction study was conducted between copper (II) and the CILs. The findings exhibit a robust linear relationship between the optical response and the concentration of the metal ion. Through the calculation of the Stern–Volmer quenching constant, it was determined that the 1:1 binding model is applicable. This research underscores the potential of UV–Vis absorption spectroscopy as a highly sensitive method for detecting metal ions. By elucidating the synthesis, photophysical behavior, and metal ion interaction of thiazolidine-based CILs, this study contributes valuable insights into the field of functionalized ionic liquids and their potential applications in various areas.
Author Bach, Mariana F.
Schneider, Paulo H.
Coelho, Felipe L.
Rodembusch, Fabiano S.
Griebeler, Cassiana H.
Silva, Henrique C.
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Cites_doi 10.1021/ic00277a030
10.1002/chem.201501679
10.1021/ja0475914
10.2174/1570179413666160818145415
10.1002/macp.202100425
10.1016/j.jlumin.2021.118401
10.1021/acs.chemrev.7b00246
10.1063/5.0004608
10.4103/2229-5186.79345
10.1039/C5RA21277D
10.1002/jcc.23266
10.1039/C6GC00415F
10.1021/ct300715s
10.1021/jp402329v
10.1038/s41467-018-03841-5
10.1021/acs.macromol.5b02193
10.1039/D0CS01087A
10.1016/j.dyepig.2022.110472
10.1366/0003702011952596
10.1016/j.progpolymsci.2018.09.004
10.1007/s11426-017-9114-4
10.1063/1.4867135
10.1002/cctc.202200916
10.1039/C9CP06869D
10.1039/D1TC05265A
10.1002/smll.201601545
10.1021/acssuschemeng.1c05129
10.1038/s41467-022-31547-2
10.1016/j.saa.2020.118431
10.1002/wcms.1327
10.1016/j.molliq.2017.04.053
10.1016/S0009-2614(99)01149-5
10.1002/wcms.81
10.1039/C5CP07134H
10.1039/b706571j
10.1039/C0CS00062K
10.1246/cl.2007.1256
10.1021/ol0616081
10.1021/cr980032t
10.1016/j.molliq.2016.11.123
10.1021/ma502160w
10.1007/s41061-020-0298-4
10.1016/j.ccr.2022.214769
10.1016/j.dyepig.2020.108566
10.1039/C6CC03888C
10.1039/b508541a
10.1021/jm701555p
10.1063/5.0006002
10.1021/acssuschemeng.6b01381
10.1080/00268976.2021.1965235
10.1016/j.molliq.2015.11.026
10.1002/aoc.5624
10.3390/molecules15042388
10.1002/ejoc.201701426
10.1016/j.jphotochemrev.2019.100338
10.1002/pola.28420
10.1016/j.molliq.2022.118556
10.1039/b716593p
10.1063/1.1558471
10.1002/anie.201504951
10.1021/ja310236m
10.3390/s17010035
10.1016/j.molliq.2019.112038
10.1021/acssuschemeng.6b00553
10.1021/jo900548f
10.1071/CH07309
10.1016/j.molliq.2020.113525
10.1063/1.456153
10.1016/j.tet.2013.09.017
10.1039/C8NJ05697H
10.3389/fchem.2021.734076
10.1007/s00253-003-1274-y
10.1021/om500123x
10.1021/acs.langmuir.6b00201
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References Avtar (ref_12) 2017; 14
Merten (ref_1) 2018; 9
Welton (ref_6) 1999; 99
Miao (ref_56) 2016; 18
Weigend (ref_31) 2005; 7
Hirata (ref_36) 1999; 314
Cravotto (ref_19) 2007; 60
Yarasir (ref_9) 2020; 34
Lee (ref_50) 2004; 126
Ogura (ref_61) 2013; 117
Vekariya (ref_13) 2017; 227
Katoh (ref_59) 2007; 36
Neese (ref_28) 2020; 152
Vishnumaya (ref_40) 2009; 74
Balakrishnan (ref_8) 2015; 5
Shrivastava (ref_25) 2011; 2
Vishnumaya (ref_41) 2006; 8
Sun (ref_52) 2012; 134
Gehlen (ref_71) 2020; 42
Borba (ref_23) 2020; 313
Mingkang (ref_51) 2021; 9
Pearson (ref_65) 1988; 27
ref_69
Pracht (ref_29) 2020; 22
Liu (ref_57) 2016; 32
Duarte (ref_70) 2020; 181
Elander (ref_2) 2003; 61
(ref_15) 2017; 236
ref_20
Yi (ref_47) 2022; 10
Aydin (ref_10) 2020; 238
Abbott (ref_64) 2008; 104
Lei (ref_5) 2017; 117
Zhang (ref_62) 2021; 239
Martin (ref_33) 2003; 118
(ref_66) 2022; 14
Fukaya (ref_18) 2007; 9
Lechner (ref_32) 2021; 119
Parker (ref_37) 2014; 140
Zhu (ref_60) 2016; 213
Li (ref_55) 2015; 48
Jordan (ref_22) 2016; 18
Gohil (ref_73) 2021; 9
ref_35
Neese (ref_26) 2012; 2
Chen (ref_68) 2022; 204
Klejdysz (ref_16) 2016; 4
Zhou (ref_48) 2016; 12
Kaur (ref_7) 2022; 351
Ji (ref_49) 2022; 13
ref_74
Tomalia (ref_45) 2019; 90
Fedorova (ref_67) 2019; 43
Nakatani (ref_3) 2008; 51
Glendening (ref_34) 2013; 34
Hulsbosch (ref_17) 2016; 4
Tang (ref_43) 2021; 50
Chatterjee (ref_72) 2015; 21
Vidal (ref_24) 2014; 33
Yuan (ref_53) 2017; 55
Neese (ref_27) 2018; 8
Suzuki (ref_14) 2013; 69
Thordarson (ref_75) 2011; 40
Zhao (ref_54) 2015; 48
Larson (ref_58) 2001; 55
Ahmad (ref_63) 2022; 472
Singh (ref_11) 2020; 297
Lin (ref_30) 2013; 9
Smith (ref_38) 2020; 152
Deng (ref_44) 2022; 223
Hibbert (ref_76) 2016; 52
Chen (ref_46) 2018; 61
Sahiba (ref_4) 2020; 378
Bach (ref_21) 2017; 2017
Dunning (ref_39) 1989; 90
Zhu (ref_42) 2015; 54
References_xml – volume: 27
  start-page: 734
  year: 1988
  ident: ref_65
  article-title: Absolute electronegativity and hardness: Application to inorganic chemistry
  publication-title: Inorg. Chem.
  doi: 10.1021/ic00277a030
  contributor:
    fullname: Pearson
– volume: 21
  start-page: 13943
  year: 2015
  ident: ref_72
  article-title: Copper(II)-specific fluorogenic task-specific ionic liquids as selective fluorescence probes and recyclable extractants
  publication-title: Chem. Eur. J.
  doi: 10.1002/chem.201501679
  contributor:
    fullname: Chatterjee
– volume: 126
  start-page: 8358
  year: 2004
  ident: ref_50
  article-title: Strong blue photoluminescence and ECL from OH-terminated PAMAM dendrimers in the absence of gold nanoparticles
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja0475914
  contributor:
    fullname: Lee
– ident: ref_74
– volume: 14
  start-page: 488
  year: 2017
  ident: ref_12
  article-title: Chiral ionic liquids: Design, synthesis and applications in asymmetric organo-catalysis
  publication-title: Curr. Org. Synth.
  doi: 10.2174/1570179413666160818145415
  contributor:
    fullname: Avtar
– volume: 223
  start-page: 2100425
  year: 2022
  ident: ref_44
  article-title: Nontraditional organic/polymeric luminogens with red-shifted fluorescence emissions
  publication-title: Macromol. Chem. Phys.
  doi: 10.1002/macp.202100425
  contributor:
    fullname: Deng
– volume: 239
  start-page: 118401
  year: 2021
  ident: ref_62
  article-title: Three distinct concentration-dependent chromophores of non-traditional intrinsic luminescence: The mechanism and special properties
  publication-title: J. Lumin.
  doi: 10.1016/j.jlumin.2021.118401
  contributor:
    fullname: Zhang
– volume: 117
  start-page: 6633
  year: 2017
  ident: ref_5
  article-title: Introduction: Ionic Liquids
  publication-title: Chem. Rev.
  doi: 10.1021/acs.chemrev.7b00246
  contributor:
    fullname: Lei
– volume: 152
  start-page: 224108
  year: 2020
  ident: ref_28
  article-title: The ORCA Quantum Chemistry Program Package
  publication-title: J. Chem. Phys.
  doi: 10.1063/5.0004608
  contributor:
    fullname: Neese
– volume: 2
  start-page: 21
  year: 2011
  ident: ref_25
  article-title: Methods for the determination of limit of detection and limit of quantitation of the analytical methods
  publication-title: Chron. Young Sci.
  doi: 10.4103/2229-5186.79345
  contributor:
    fullname: Shrivastava
– volume: 5
  start-page: 105453
  year: 2015
  ident: ref_8
  article-title: Fluorescence response of a thiazolidine carboxylic acid derivative for the selective and nanomolar detection of Zn(II) ions: Quantum chemical calculations and application in real samples
  publication-title: RSC Adv.
  doi: 10.1039/C5RA21277D
  contributor:
    fullname: Balakrishnan
– volume: 34
  start-page: 1429
  year: 2013
  ident: ref_34
  article-title: NBO 6.0: Natural Bond Orbital Analysis Program
  publication-title: J. Comput. Chem.
  doi: 10.1002/jcc.23266
  contributor:
    fullname: Glendening
– volume: 18
  start-page: 4374
  year: 2016
  ident: ref_22
  article-title: Synthesis of a series of amino acid derived ionic liquids and tertiary amines: Green chemistry metrics including microbial toxicity and preliminary biodegradation data analysis
  publication-title: Green Chem.
  doi: 10.1039/C6GC00415F
  contributor:
    fullname: Jordan
– volume: 9
  start-page: 263
  year: 2013
  ident: ref_30
  article-title: Long-Range Corrected Hybrid Density Functionals with Improved Dispersion Corrections
  publication-title: J. Chem. Theory Comput.
  doi: 10.1021/ct300715s
  contributor:
    fullname: Lin
– ident: ref_35
– volume: 117
  start-page: 8547
  year: 2013
  ident: ref_61
  article-title: Charge-transfer electronic absorption spectra of 1-ethylpyridinium cation and halogen anion pairs in dichloromethane and as neat ionic liquids
  publication-title: J. Phys. Chem. B
  doi: 10.1021/jp402329v
  contributor:
    fullname: Ogura
– volume: 9
  start-page: 1949
  year: 2018
  ident: ref_1
  article-title: Enantioselective reduction of sulfur-containing cyclic imines through biocatalysis
  publication-title: Nat. Commun.
  doi: 10.1038/s41467-018-03841-5
  contributor:
    fullname: Merten
– volume: 48
  start-page: 7747
  year: 2015
  ident: ref_55
  article-title: Catalyst-free, atom-economic, multicomponent polymerizations of aromatic diynes, elemental sulfur, and aliphatic diamines toward luminescent polythioamides
  publication-title: Macromolecules
  doi: 10.1021/acs.macromol.5b02193
  contributor:
    fullname: Li
– volume: 50
  start-page: 12616
  year: 2021
  ident: ref_43
  article-title: Nonconventional luminophores: Characteristics, advancements and perspectives
  publication-title: Chem. Soc. Rev.
  doi: 10.1039/D0CS01087A
  contributor:
    fullname: Tang
– volume: 204
  start-page: 110472
  year: 2022
  ident: ref_68
  article-title: A lysosome-targeted near-infrared fluorescent probe for cell imaging of Cu2+
  publication-title: Dyes Pigm.
  doi: 10.1016/j.dyepig.2022.110472
  contributor:
    fullname: Chen
– volume: 55
  start-page: 679
  year: 2001
  ident: ref_58
  article-title: Intrinsic fluorescence of carboxylated-terminated polyamido amine dendrimers
  publication-title: Appl. Spectrosc. Rev.
  doi: 10.1366/0003702011952596
  contributor:
    fullname: Larson
– volume: 90
  start-page: 35
  year: 2019
  ident: ref_45
  article-title: Non-traditional intrinsic luminescence: Inexplicable blue fluorescence observed for dendrimers, macromolecules and small molecular structures lacking traditional/conventional luminophores
  publication-title: Progr. Polym. Sci.
  doi: 10.1016/j.progpolymsci.2018.09.004
  contributor:
    fullname: Tomalia
– volume: 61
  start-page: 351
  year: 2018
  ident: ref_46
  article-title: Prevalent intrinsic emission from nonaromatic amino acids and poly(amino acids)
  publication-title: Sci. China Chem.
  doi: 10.1007/s11426-017-9114-4
  contributor:
    fullname: Chen
– volume: 140
  start-page: 094106
  year: 2014
  ident: ref_37
  article-title: Levels of Symmetry Adapted Perturbation Theory (SAPT). I. Efficiency and performance for interaction energies
  publication-title: J. Chem. Phys.
  doi: 10.1063/1.4867135
  contributor:
    fullname: Parker
– volume: 14
  start-page: e202200916
  year: 2022
  ident: ref_66
  article-title: Ligand-to-metal charge transfer (LMCT) photochemistry at 3d-metal complexes: An emerging tool for sustainable organic synthesis
  publication-title: ChemCatChem
  doi: 10.1002/cctc.202200916
– volume: 22
  start-page: 7169
  year: 2020
  ident: ref_29
  article-title: Automated Exploration of the Low-Energy Chemical Space with Fast Quantum Chemical Methods
  publication-title: Phys. Chem. Chem. Phys.
  doi: 10.1039/C9CP06869D
  contributor:
    fullname: Pracht
– volume: 10
  start-page: 1645
  year: 2022
  ident: ref_47
  article-title: Ionic liquid crystals based on amino acids and gemini surfactants: Tunable phase structure, circularly polarized luminescence and emission color
  publication-title: J. Mater. Chem. C
  doi: 10.1039/D1TC05265A
  contributor:
    fullname: Yi
– volume: 12
  start-page: 6586
  year: 2016
  ident: ref_48
  article-title: Clustering-triggered emission of nonconjugated polyacrylonitrile
  publication-title: Small
  doi: 10.1002/smll.201601545
  contributor:
    fullname: Zhou
– volume: 9
  start-page: 13096
  year: 2021
  ident: ref_73
  article-title: Sensing vs. extraction: Functionalized ionic liquid as a single platform for dual applications with biological implications
  publication-title: ACS Sustain. Chem. Eng.
  doi: 10.1021/acssuschemeng.1c05129
  contributor:
    fullname: Gohil
– volume: 13
  start-page: 3717
  year: 2022
  ident: ref_49
  article-title: Anionic polymerization of nonaromatic maleimide to achieve full-color nonconventional luminescence
  publication-title: Nat. Commun.
  doi: 10.1038/s41467-022-31547-2
  contributor:
    fullname: Ji
– volume: 238
  start-page: 118431
  year: 2020
  ident: ref_10
  article-title: Thiazolidine based fluorescent chemosensors for aluminum ions and their applications in biological imaging
  publication-title: Spectrochim. Acta A
  doi: 10.1016/j.saa.2020.118431
  contributor:
    fullname: Aydin
– volume: 8
  start-page: e1327
  year: 2018
  ident: ref_27
  article-title: Software Update: The ORCA Program System, version 4.0
  publication-title: WIREs Comput. Mol. Sci.
  doi: 10.1002/wcms.1327
  contributor:
    fullname: Neese
– volume: 236
  start-page: 435
  year: 2017
  ident: ref_15
  article-title: Physical-chemical properties of chiral ionic liquids derived from the phenylethylamine enantiomers
  publication-title: J. Mol. Liq.
  doi: 10.1016/j.molliq.2017.04.053
– volume: 314
  start-page: 291
  year: 1999
  ident: ref_36
  article-title: Time-Dependent Density Functional Theory within the Tamm–Dancoff Approximation
  publication-title: Chem. Phys. Lett.
  doi: 10.1016/S0009-2614(99)01149-5
  contributor:
    fullname: Hirata
– volume: 2
  start-page: 73
  year: 2012
  ident: ref_26
  article-title: The ORCA Program System
  publication-title: WIREs Comput. Mol. Sci.
  doi: 10.1002/wcms.81
  contributor:
    fullname: Neese
– volume: 18
  start-page: 4295
  year: 2016
  ident: ref_56
  article-title: Fluorescent aliphatic hyperbranched polyether: Chromophore-free and without any N and P atoms
  publication-title: Phys. Chem. Chem. Phys.
  doi: 10.1039/C5CP07134H
  contributor:
    fullname: Miao
– volume: 9
  start-page: 1155
  year: 2007
  ident: ref_18
  article-title: Bio ionic liquids: Room temperature ionic liquids composed wholly of biomaterials
  publication-title: Green Chem.
  doi: 10.1039/b706571j
  contributor:
    fullname: Fukaya
– volume: 40
  start-page: 1305
  year: 2011
  ident: ref_75
  article-title: Determining association constants from titration experiments in supramolecular chemistry
  publication-title: Chem. Soc. Rev.
  doi: 10.1039/C0CS00062K
  contributor:
    fullname: Thordarson
– volume: 36
  start-page: 1256
  year: 2007
  ident: ref_59
  article-title: Absorption spectra of imidazolium ionic liquids
  publication-title: Chem. Lett.
  doi: 10.1246/cl.2007.1256
  contributor:
    fullname: Katoh
– volume: 8
  start-page: 4097
  year: 2006
  ident: ref_41
  article-title: Highly enantioselective direct aldol reaction catalyzed by organic molecules
  publication-title: Org. Lett.
  doi: 10.1021/ol0616081
  contributor:
    fullname: Vishnumaya
– volume: 99
  start-page: 2071
  year: 1999
  ident: ref_6
  article-title: Room-temperature ionic liquids. Solvents for synthesis and catalysis
  publication-title: Chem. Rev.
  doi: 10.1021/cr980032t
  contributor:
    fullname: Welton
– volume: 227
  start-page: 44
  year: 2017
  ident: ref_13
  article-title: A review of ionic liquids: Applications towards catalytic organic transformations
  publication-title: J. Mol. Liq.
  doi: 10.1016/j.molliq.2016.11.123
  contributor:
    fullname: Vekariya
– volume: 48
  start-page: 64
  year: 2015
  ident: ref_54
  article-title: Poly[(maleic anhydride)-alt-(vinyl acetate)]: A pure oxygenic nonconjugated macro-molecule with strong light emission and solvatochromic effect
  publication-title: Macromolecules
  doi: 10.1021/ma502160w
  contributor:
    fullname: Zhao
– volume: 378
  start-page: 34
  year: 2020
  ident: ref_4
  article-title: Saturated five membered thiazolidines and their derivatives: From synthesis to biological applications
  publication-title: Top. Curr. Chem.
  doi: 10.1007/s41061-020-0298-4
  contributor:
    fullname: Sahiba
– volume: 472
  start-page: 214769
  year: 2022
  ident: ref_63
  article-title: Ionic liquid coordinated metal-catalyzed organic transformations: A comprehensive review
  publication-title: Coord. Chem. Rev.
  doi: 10.1016/j.ccr.2022.214769
  contributor:
    fullname: Ahmad
– volume: 181
  start-page: 108566
  year: 2020
  ident: ref_70
  article-title: A selective proton transfer optical sensor for copper II based on chelation enhancement quenching effect (CHEQ)
  publication-title: Dyes Pigm.
  doi: 10.1016/j.dyepig.2020.108566
  contributor:
    fullname: Duarte
– volume: 52
  start-page: 12792
  year: 2016
  ident: ref_76
  article-title: The death of the Job plot, transparency, open science and online tools, uncertainty estimation methods and other developments in supramolecular chemistry data analysis
  publication-title: Chem. Commun.
  doi: 10.1039/C6CC03888C
  contributor:
    fullname: Hibbert
– volume: 7
  start-page: 3297
  year: 2005
  ident: ref_31
  article-title: Balanced Basis Sets of Split Valence, Triple Zeta Valence and Quadruple Zeta Valence Quality for H to Rn: Design and Assessment of Accuracy
  publication-title: Phys. Chem. Chem. Phys.
  doi: 10.1039/b508541a
  contributor:
    fullname: Weigend
– volume: 51
  start-page: 2992
  year: 2008
  ident: ref_3
  article-title: Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV
  publication-title: J. Med. Chem.
  doi: 10.1021/jm701555p
  contributor:
    fullname: Nakatani
– volume: 152
  start-page: 184108
  year: 2020
  ident: ref_38
  article-title: Psi4 1.4: Open-source software for high-throughput quantum chemistry
  publication-title: J. Chem. Phys.
  doi: 10.1063/5.0006002
  contributor:
    fullname: Smith
– volume: 4
  start-page: 6543
  year: 2016
  ident: ref_16
  article-title: Biobased ionic liquids with abietate anion
  publication-title: ACS Sustain. Chem. Eng.
  doi: 10.1021/acssuschemeng.6b01381
  contributor:
    fullname: Klejdysz
– volume: 119
  start-page: 21
  year: 2021
  ident: ref_32
  article-title: An excited state coupled-cluster study on indigo dyes
  publication-title: Mol. Phys.
  doi: 10.1080/00268976.2021.1965235
  contributor:
    fullname: Lechner
– volume: 213
  start-page: 289
  year: 2016
  ident: ref_60
  article-title: Interactions between pyrene and pyridinium ionic liquids studied by ultraviolet–visible spectroscopy
  publication-title: J. Mol. Liq.
  doi: 10.1016/j.molliq.2015.11.026
  contributor:
    fullname: Zhu
– volume: 34
  start-page: e5624
  year: 2020
  ident: ref_9
  article-title: Turn-on fluorescent probe for Zn2+ ions based on thiazolidine derivative
  publication-title: Appl. Organometal. Chem.
  doi: 10.1002/aoc.5624
  contributor:
    fullname: Yarasir
– ident: ref_20
  doi: 10.3390/molecules15042388
– volume: 2017
  start-page: 6997
  year: 2017
  ident: ref_21
  article-title: Design of a chiral ionic liquid system for the enantioselective addition of diethylzinc to aldehydes
  publication-title: Eur. J. Org. Chem.
  doi: 10.1002/ejoc.201701426
  contributor:
    fullname: Bach
– volume: 42
  start-page: 100338
  year: 2020
  ident: ref_71
  article-title: The centenary of the Stern-Volmer equation of fluorescence quenching: From the single line plot to the SV quenching map
  publication-title: J. Photochem. Photobiol. C Photochem. Rev.
  doi: 10.1016/j.jphotochemrev.2019.100338
  contributor:
    fullname: Gehlen
– volume: 55
  start-page: 560
  year: 2017
  ident: ref_53
  article-title: Nonconventional macromolecular luminogens with aggregation-induced emission characteristics
  publication-title: J. Polym. Sci. Part A Polym. Chem.
  doi: 10.1002/pola.28420
  contributor:
    fullname: Yuan
– volume: 351
  start-page: 118556
  year: 2022
  ident: ref_7
  article-title: Diverse applications of ionic liquids: A comprehensive review
  publication-title: J. Mol. Liq.
  doi: 10.1016/j.molliq.2022.118556
  contributor:
    fullname: Kaur
– volume: 104
  start-page: 21
  year: 2008
  ident: ref_64
  article-title: Metal complexation in ionic liquids
  publication-title: Annu. Rep. Prog. Chem. Sect. A Inorg. Chem.
  doi: 10.1039/b716593p
  contributor:
    fullname: Abbott
– volume: 118
  start-page: 4775
  year: 2003
  ident: ref_33
  article-title: Natural transition orbitals
  publication-title: J. Chem. Phys.
  doi: 10.1063/1.1558471
  contributor:
    fullname: Martin
– volume: 54
  start-page: 14626
  year: 2015
  ident: ref_42
  article-title: Non-conjugated polymer dots with crosslink-enhanced emission in the absence of fluorophore units
  publication-title: Angew. Chem. Int. Ed.
  doi: 10.1002/anie.201504951
  contributor:
    fullname: Zhu
– volume: 134
  start-page: 20581
  year: 2012
  ident: ref_52
  article-title: A unique aliphatic tertiary amine chromophore: Fluorescence, polymer structure, and application in cell imaging
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja310236m
  contributor:
    fullname: Sun
– ident: ref_69
  doi: 10.3390/s17010035
– volume: 297
  start-page: 112038
  year: 2020
  ident: ref_11
  article-title: Ionic liquids synthesis and applications: An overview
  publication-title: J. Mol. Liq.
  doi: 10.1016/j.molliq.2019.112038
  contributor:
    fullname: Singh
– volume: 4
  start-page: 2917
  year: 2016
  ident: ref_17
  article-title: Biobased ionic liquids: Solvents for a green processing industry?
  publication-title: ACS Sustain. Chem. Eng.
  doi: 10.1021/acssuschemeng.6b00553
  contributor:
    fullname: Hulsbosch
– volume: 74
  start-page: 4289
  year: 2009
  ident: ref_40
  article-title: Highly efficient small organic molecules for enantioselective direct aldol reaction in organic and aqueous media
  publication-title: J. Org. Chem.
  doi: 10.1021/jo900548f
  contributor:
    fullname: Vishnumaya
– volume: 60
  start-page: 946
  year: 2007
  ident: ref_19
  article-title: A speedy one-pot synthesis of second-generation ionic liquids under ultrasound and/or microwave irradiation
  publication-title: Aust. J. Chem.
  doi: 10.1071/CH07309
  contributor:
    fullname: Cravotto
– volume: 313
  start-page: 113525
  year: 2020
  ident: ref_23
  article-title: Non-traditional intrinsic luminescence of amphiphilic-based ionic liquids from oxazolidines: Interaction studies in phosphatidylcholine-composed liposomes and BSA optical sensing in solution
  publication-title: J. Mol. Liq.
  doi: 10.1016/j.molliq.2020.113525
  contributor:
    fullname: Borba
– volume: 90
  start-page: 1007
  year: 1989
  ident: ref_39
  article-title: Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen
  publication-title: J. Chem. Phys.
  doi: 10.1063/1.456153
  contributor:
    fullname: Dunning
– volume: 69
  start-page: 9690
  year: 2013
  ident: ref_14
  article-title: Imidazolium-based chiral ionic liquids: Synthesis and application
  publication-title: Tetrahedron
  doi: 10.1016/j.tet.2013.09.017
  contributor:
    fullname: Suzuki
– volume: 43
  start-page: 2817
  year: 2019
  ident: ref_67
  article-title: Intramolecular electron transfer in Cu(II) complexes with aryl-imidazo-1,10-phenanthroline derivatives: Experimental and quantum chemical calculation studies
  publication-title: New J. Chem.
  doi: 10.1039/C8NJ05697H
  contributor:
    fullname: Fedorova
– volume: 9
  start-page: 734076
  year: 2021
  ident: ref_51
  article-title: Assemblies of polyacrylonitrile-derived photoactive polymers as blue and green light photo-cocatalysts for Cu-catalyzed ATRP in water and organic solvents
  publication-title: Front. Chem.
  doi: 10.3389/fchem.2021.734076
  contributor:
    fullname: Mingkang
– volume: 61
  start-page: 385
  year: 2003
  ident: ref_2
  article-title: Industrial production of β-lactam antibiotics
  publication-title: Appl. Microbiol. Biotechnol.
  doi: 10.1007/s00253-003-1274-y
  contributor:
    fullname: Elander
– volume: 33
  start-page: 3328
  year: 2014
  ident: ref_24
  article-title: Thermophysical properties of imidazolium-functionalized binols and their application in asymmetric catalysis
  publication-title: Organometallics
  doi: 10.1021/om500123x
  contributor:
    fullname: Vidal
– volume: 32
  start-page: 1881
  year: 2016
  ident: ref_57
  article-title: pH-mediated fluorescent polymer particles and gel from hyperbranched polyethylenimine and the mechanism of intrinsic fluorescence
  publication-title: Langmuir
  doi: 10.1021/acs.langmuir.6b00201
  contributor:
    fullname: Liu
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Snippet This study presents a comprehensive analysis of the synthesis and photophysical properties of thiazolidine-functionalized chiral ionic liquids (CILs) derived...
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SubjectTerms ionic liquids
optical sensor
thiazolidines
Title Thiazolidine-Based Fluorescent Chiral Ionic Liquids for Trace Copper(II) Ion Sensing
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