A new 7-(diethylamino)coumarin and 4-(diethylamino)phenol appended unsymmetrical thiocarbohydrazone: Detection of moisture in organic solvent and sequential fluorimetric detection of Cu2+ ions and cysteine

Santhiya, Kuppusamy; Mathivanan, Moorthy; Tharmalingam, Balamurugan; Anitha, Ottoor; Ghorai, Sandipan; Natarajan, Ramalingam; Murugesapandian, Balasubramanian

doi:10.1016/j.jphotochem.2022.114105

Cited by 10 publications

(7 citation statements)

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“…In this context, the application of ESIPT-fluorophores for a plethora of sensing purposes has become one of the mainstream interdisciplinary directions fusing together analytical, organic and physical chemistry. [56][57][58][59][60][61][62][63][64][65][66][67][68] Although the molecules of ESIPT-fluorophores can bind metal ions (which is used for the detection of metals), this phenomenon is typically coupled with their deprotonation and the disappearance of ESIPT in the metal complex molecules (Scheme 2, top). [69][70][71][72][73][74][75][76] Nevertheless, the purposeful design of specific sites for metal coordination in the molecules of ESIPT-fluorophores paves the way toward metal ion binding without the deprotonation of ESIPT-fluorophores (Scheme 2, bottom).…”

Section: Introductionmentioning

confidence: 99%

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Tuning ESIPT-coupled luminescence by expanding π-conjugation of a proton acceptor moiety in ESIPT-capable zinc(ii) complexes with 1-hydroxy-1H-imidazole-based ligands

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tuning ESIPT-coupled luminescence by expanding π-conjugation of a proton acceptor moiety in ESIPT-capable zinc(ii) complexes with 1-hydroxy-1H-imidazole-based ligands

et al. 2022

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“…The ESIPT photoreaction ( Scheme 1 ) is highly sensitive to substituents [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ] and coordinated metal ions [ 28 , 29 , 30 , 31 , 32 , 33 ], protonation/deprotonation [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ], the state of aggregation [ 42 , 43 ], the polarity of solvent [ 44 , 45 , 46 , 47 , 48 ] and the presence of various analytes [ 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 ]. If the excited state tautomerization (normal-to-tautomeric) is barrierless, the only form to emit is the tautomeric one, which typically luminesces with rather large Stokes shift [ 57 , 58 ].…”

Section: Introductionmentioning

confidence: 99%

ESIPT-Capable 4-(2-Hydroxyphenyl)-2-(Pyridin-2-yl)-1H-Imidazoles with Single and Double Proton Transfer: Synthesis, Selective Reduction of the Imidazolic OH Group and Luminescence

et al. 2023

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1H-Imidazole derivatives establish one of the iconic classes of ESIPT-capable compounds (ESIPT = excited state intramolecular proton transfer). This work presents the synthesis of 1-hydroxy-4-(2-hydroxyphenyl)-5-methyl-2-(pyridin-2-yl)-1H-imidazole (LOH,OH) as the first example of ESIPT-capable imidazole derivatives wherein the imidazole moiety simultaneously acts as a proton acceptor and a proton donor. The reaction of LOH,OH with chloroacetone leads to the selective reduction of the imidazolic OH group (whereas the phenolic OH group remains unaffected) and to the isolation of 4-(2-hydroxyphenyl)-5-methyl-2-(pyridin-2-yl)-1H-imidazole (LH,OH), a monohydroxy congener of LOH,OH. Both LOH,OH and LH,OH demonstrate luminescence in the solid state. The number of OH···N proton transfer sites in these compounds (one for LH,OH and two for LOH,OH) strongly affects the luminescence mechanism and color of the emission: LH,OH emits in the light green region, whereas LOH,OH luminesces in the orange region. According to joint experimental and theoretical studies, the main emission pathway of both compounds is associated with T1 → S0 phosphorescence and not related to ESIPT. At the same time, LOH,OH also exhibits S1 → S0 fluorescence associated with ESIPT with one proton transferred from the hydroxyimidazole moiety to the pyridine moiety, which is not possible for LH,OH due to the absence of the hydroxy group in the imidazole moiety.

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“…Murugesapandian et al 49 developed coumarin-derived unsymmetrical thiocarbohyrazone 21 for moisture, Cu 2+ and Cys sensing (Fig. 16).…”

Section: Introductionmentioning

confidence: 99%

ESIPT-based probes for cations, anions and neutral species: recent progress, multidisciplinary applications and future perspectives

Nehra,

Kaushik

2023

Anal. Methods

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A new 7-(diethylamino)coumarin and 4-(diethylamino)phenol appended unsymmetrical thiocarbohydrazone: Detection of moisture in organic solvent and sequential fluorimetric detection of Cu2+ ions and cysteine

Cited by 10 publications

References 69 publications

Tuning ESIPT-coupled luminescence by expanding π-conjugation of a proton acceptor moiety in ESIPT-capable zinc(ii) complexes with 1-hydroxy-1H-imidazole-based ligands

Tuning ESIPT-coupled luminescence by expanding π-conjugation of a proton acceptor moiety in ESIPT-capable zinc(ii) complexes with 1-hydroxy-1H-imidazole-based ligands

ESIPT-Capable 4-(2-Hydroxyphenyl)-2-(Pyridin-2-yl)-1H-Imidazoles with Single and Double Proton Transfer: Synthesis, Selective Reduction of the Imidazolic OH Group and Luminescence

ESIPT-based probes for cations, anions and neutral species: recent progress, multidisciplinary applications and future perspectives

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