Investigation of substitution effect on fluorescence properties of Zn2+-selective ratiometric fluorescent compounds: 2-(2′-Hydroxyphenyl)benzimidazole derivatives

Akutsu, Kazuhiro; Mori, Susumu; Shinmei, Kenichi; Iwase, Hiroki; Nakano, Yoshiharu; Fujii, Yuki

doi:10.1016/j.talanta.2015.09.001

Cited by 25 publications

(11 citation statements)

References 57 publications

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“…10 nm. This small shift can be related to the presence of electron withdrawing groups (–Cl, –Br and I) that decreases the Highest Occupied Molecular Orbital-Lowest Unoccupied Molecular Orbital (HOMO-LUMO) energy gap of substituted derivatives [ 40 , 41 ]. In these kind of compounds, ESIPT is strongly influenced by the nature and position of the substituents, which adjust the strength of the hydrogen bond [ 42 , 43 , 44 ].…”

Section: Resultsmentioning

confidence: 99%

Benzimidazole-Based N,O Boron Complexes as Deep Blue Solid-State Fluorophores

et al. 2021

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Benzimidazole-based boranils were designed and synthesized in order to assess the influence of halogen substituents on their optoelectronic properties. All compounds are photoluminescent in solution and solid state. Compared to the free ligands, the new boranils emit at a lower wavelength, by elimination of the excited-state intramolecular proton transfer observed with the ligands. In the solid state, some of the boranils exhibit a deep blue emission, presenting Commission Internationale de l’Éclairage (CIE) coordinates with an x-component of less than 0.16 and a y-component smaller than 0.04, highly desired values for the development of blue emitting materials.

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Section: Resultsmentioning

confidence: 99%

Benzimidazole-Based N,O Boron Complexes as Deep Blue Solid-State Fluorophores

et al. 2021

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“…The absorption maxima of HBT, HBO, and HBI is in the range of 330–355 nm, while HBT exhibits enol emission around 390 nm and keto emission at 512 nm whereas HBO and HBI exhibit only keto emission at 480 nm and 460 nm respectively (see Table ). Hence without any substituents, HBX emits in blue to green region.…”

Section: Synthetic and Photophysical Methodologies Of Hydroxybenzazolmentioning

confidence: 99%

Towards NIR‐Active Hydroxybenzazole (HBX)‐Based ESIPT Motifs: A Recent Research Trend

2020

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In this review, we have explored the synthetic strategies adopted for designing the hydroxybenzazoles (imidazole, oxazole, and thiazole) i. e. HBX derivatives which show emission in red and NIR region. Further, we have examined the effect of different substituents i. e. either directly attached or with extended conjugation on a phenolic ring/ phenyl ring of heterocycles to achieve a red to NIR shift in emission. Finally, we have investigated the applications and computational methodologies adopted for red to NIR emitting dyes. In the future, this review will help to design, synthesized and examine the applications of new derivatives of HBX which will show emission in red to NIR region.

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“…These maximum are similar to 2-(m-methylphenyl)benzimidazole, 2-(p-methylphenyl)benzimidazole, 2-(m-methoxyphenyl)benzimidazole, 2-(pmethoxyphenyl)benzimidazole. But the 2-(o-hydroxyphenyl)benzimidazole molecule is observed the specific property in the ground and excited states to describe the keto-enol tautomeric equilibrium through the excited state intramolecular proton transfer [58][59][60][61][62][63][64][65], which property already given in introduction part and theoretical study also done for ketoenol tautomer in solvent effect. The absorption maximum of 2-(o-hydroxyphenyl)benzimidazole was observed at 335, 318 and 295 nm and fluorescence maximum at 355 and 465 nm in DMSO [32].…”

Section: Absorption and Emission Spectral Studymentioning

confidence: 99%

Spectral and Theoretical Studies of Benzimidazole and 2-Phenyl Substituted Benzimidazoles

Prabhu¹

2022

Benzimidazole

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This chapter discusses about the spectral and theoretical aspects of selected benzimidazole and 2-phenyl substituted benzimidazole molecules. The synthesis of these benzimidazoles was reported in many methods by the reaction between o-phenylenediamine with formic acid, aromatic aldehydes and N-benzylbezene-1,2-diamine in presence of oxidant tert-butyl hydroperoxide (TBHP). The spectral analysis of these molecules mainly such as UV-visible, fluorescence in solvents will be included in this chapter and discussed about the absorption, fluorescence maximum, conjugation, transition. Further the optimized structure of these molecules will be given using Gaussian 09 W (DFT 6-31G method). And also will be discussed about structural parameters, highest occupied molecular orbital (HOMO) – lowest unoccupied molecular orbital (LUMO) energy energy values, natural bond orbital (NBO), molecular electrostatic potential map (ESP). Many benzimidazole molecules having tautomers in the structure will be explained with the help of theoretical parameters to describe the structural properties.

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Investigation of substitution effect on fluorescence properties of Zn2+-selective ratiometric fluorescent compounds: 2-(2′-Hydroxyphenyl)benzimidazole derivatives

Cited by 25 publications

References 57 publications

Benzimidazole-Based N,O Boron Complexes as Deep Blue Solid-State Fluorophores

Benzimidazole-Based N,O Boron Complexes as Deep Blue Solid-State Fluorophores

Towards NIR‐Active Hydroxybenzazole (HBX)‐Based ESIPT Motifs: A Recent Research Trend

Spectral and Theoretical Studies of Benzimidazole and 2-Phenyl Substituted Benzimidazoles

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