Effectively controlling the ESIPT behavior and fluorescence feature of 2-(2′-hydroxyphenyl)-4-chloromethylthiazole by changing its π-conjugation: A theoretical exploration

Su, Shenyang; Sun, Guotao; Liang, Xiuning; Fang, Hua

doi:10.1016/j.jphotochem.2021.113548

Cited by 12 publications

(8 citation statements)

References 67 publications

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“…105,106,119 It is well known that the proton transfer abilities and emission properties of ESIPT-capable molecules can be tuned by substitution on the proton-donating and protonaccepting cores, as well as by the degree of π-conjugation. [120][121][122][123][124][125][126][127][128][129][130][131][132][133][134][135][136] As far as the degree of π-conjugation is concerned, extending the π-conjugated system on the protondonating part of the molecule can frustrate the ESIPT process, since the excited state is located predominantly on the ESIPT-incapable part of the molecule and involves the ESIPT site only to a small extent. 135,136 Instead, the extension of the π-conjugated system on the proton-accepting moiety could facilitate the ESIPT process due to better delocalization of a positive charge.…”

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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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 optical and optoelectronic properties of newly designed dyes are defined by the density variation (Fig. 1) of their frontier molecular orbitals [34]. The lowest unoccupied molecular orbital (LUMO)…”

Section: Molecular Orbitalsmentioning

confidence: 99%

Theoretical Design of Efficient Small Molecules with sp2 Hybridized Nitrogen at Varying Positions for Organic Pull Push (ON/OFF) Solar Switches

Hassan

Sumrra

Mohyuddin³

et al. 2022

Preprint

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The efficacy of specific molecular acceptors in photovoltaic devices is determined by their chemical composition. Multiscale computations are required to protect investigation design and, as a result, efforts and money are saved. Using multiscale computer simulations, the influence of sp2-hybridized nitrogen substitutions at the interior or outer location of the internal center, carbonyl group, and terminating group of specific molecular acceptors is explored. The electronic behavior is studied using quantum molecular modeling. End-capping with nitrogen has greatly reduced the energy of electron rearrangement. The transfer integral plus excited state behavior shows a significant difference. Nitrogen alteration at the terminating group location, on the other hand, is an effective approach to boost electronic conductivity. The characteristics of the acceptor with their composites with 2,2'-((4-heptyl-4,9,9-trihexyl-4,9-dihydro-s-indaceno[1,2-b:5,6-b']dithiophene-2,7-diyl)bis(methanylylidene)bis(3-oxo-2,3-dihydro-1H-indene-1-yl-2-ylidene)dimalononitrile (IDIC) donor are also investigated using molecular dynamics. To investigate the mixing of specified specific molecular acceptors is determined. According to the radial distribution function, idic4 has a tighter packing alongside IDIC3 and IDIC4. Nitrogen modification at end capping has been discovered by all analyses.

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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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Effectively controlling the ESIPT behavior and fluorescence feature of 2-(2′-hydroxyphenyl)-4-chloromethylthiazole by changing its π-conjugation: A theoretical exploration

Cited by 12 publications

References 67 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

Theoretical Design of Efficient Small Molecules with sp2 Hybridized Nitrogen at Varying Positions for Organic Pull Push (ON/OFF) Solar Switches

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

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