Azo dyes with ESIPT core for textile applications and DFT study

Ramugade, Supriya H.; Warde, Umesh; Sekar, Nagaiyan

doi:10.1016/j.dyepig.2019.107626

Cited by 31 publications

(9 citation statements)

References 20 publications

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“…Dyes that access the cis isomer thermally revert to the trans configuration. Lifetimes measured for this process vary from minutes (2,3,4) to hours (1). The lifetime of the cis configuration decreases as the log of the reversion time with the increasing value of the Hammett parameter with the most electron-donating substituent (-NMe 2 ) resulting in the shortest-lived cis-isomer.…”

Section: Discussionmentioning

confidence: 99%

“…Azo dyes are the single most commonly utilized dyes in industrial processes, 1 found in everything from food colorants and cosmetic additives 2 to textile reagents, 3 biologic indicators, 4 and organic synthons. 5 In addition, their light-driven reactivities such as the trans / cis isomerization and proton-transfer induced tautomerization have made them good candidates in the applications of functional materials, electronic devices and drug delivery.…”

Section: Introductionmentioning

confidence: 99%

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Ultra-fast excited-state dynamics of substituted trans-naphthalene azo moieties

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Huang

Martin

et al. 2023

Phys. Chem. Chem. Phys.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ultra-fast excited-state dynamics of substituted trans-naphthalene azo moieties

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Huang

Martin

et al. 2023

Phys. Chem. Chem. Phys.

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“…Excited-state proton transfer (ESPT) plays a key role in natural and artificial chemical and biological systems and has been continuously attractive to a broad scientific community for decades. − In general, proton transfer is a type of acid–base reaction in which acidic (low p K a ) and basic (high p K a ) moieties act as proton donors and acceptors, respectively. For ESPT reactions, photoacids are usually regarded as effective proton donors, which exhibit stronger acidity in excited states than in the ground state, i.e., p K a * < p K a . − The solvent molecules surrounding photoacids tend to be corresponding proton acceptors. − …”

Section: Introductionmentioning

confidence: 99%

Excited-State Proton Transfer from Embedded Photoacids to Silanols on Mesostructured Surfaces: Role of Structural Heterogeneity

et al. 2023

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As a common process in nature, excited-state proton transfer (ESPT) is becoming increasingly attractive due to its wide applications in smart sensors and materials. Compared with well-known ESPT in bulk solution, knowledge of ESPT between excited-state photoacids and silanols on mesostructured surfaces is still limited. Herein, we present our work on ESPT behavior in photoacid-embedded mesostructured CTAB−silica films by using steady and picosecond time-resolved fluorescence spectroscopy. Compared with ESPT in solutions, two unique characteristics of photoacid−silanol ESPT were revealed: (1) deprotonated silanols act as ESPT acceptors, while protonated silanols affect ESPT by changing the basicity of the silica surface; (2) largely distinguished properties of Q 3 /Q 2 silanols and their non-uniform distribution on the surface lead to heterogeneous properties of the surface such as basicity that greatly affect ESPT dynamics. Our work provides new insight into the ESPT mechanism in mesostructured systems and inspiration for designing smart sensors and materials that utilize the sensitivity to proton concentration.

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“…Osman in 2017 theoretically studied the structure, reactivity, and optical properties of thiazole azo dyes by applying B3LYP, CAM-B3LYP, and wB97XD functionals with 6-311 ++ G** and aug-cc-pvdz basis sets [12,18]. Shinde and Sekar employed computational DFT to predict the stability of tautomeric forms of the 4-hydroxyl-1-methyl-2(1H)-quinolone azo dyes and found out the electrophilicity index of prepared dyes using TD-DFT/6-31 g(d) theory level [19,20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, DFT, and TD-DFT studies of (E)-5-((4,6-dichloro-1,3,5-triazin-2-yl)amino)-4-hydroxy-3-(phenyldiazenyl)naphthalene-2,7-diylbis(hydrogen sulfite)

et al. 2021

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In this study, (E)-5-((4,6-dichloro-1,3,5-triazin-2-yl)amino)-4-hydroxy-3-(phenyldiazenyl)naphthalene-2,7-diylbis(hydrogen sulfite), a cyanurated H-acid (CHA) azo dye, was synthesized and characterized using FT-IR spectrophotometer and GC-MS spectroscopy. A density functional theory (DFT) based B3LYP and CAM-B3LYP method with 6–311 + G (d,p) basis set analysis was computed for HOMO-LUMO, natural bonding orbitals (NBO), UV-Vis absorptions and excitation interactions, in order to understand its molecular orbital excitation properties. A low Energy gap (Eg) of 2.947 eV was obtained from the molecular orbital analysis, which showed that HOMO to LUMO transition is highly feasible; hence CHA is adequate for diverse electronic and optic applications. Studies of the first five excitations (S0 → S1/S2/S3/S4/S5) of CHA revealed that S0 → S1 and S0 → S3 are π → π* type local excitations distributed around the –N=N– group; S0 → S2, a Rydberg type local excitation; S0 → S4, a highly localized π → π* excitation; while S0 → S5 is an n → π* charge transfer from a benzene ring to –N=N– group. From NBO analysis, we obtained the various donor–acceptor orbital interactions contributing to the stabilization of the studied compound. Most significantly, some strong hyper-conjugations (n → n*) within fragments, and non-bondingand anti-bonding intermolecular (n → n*/π* and π → n*/π*) interactions were observed to contribute appreciable energies. This study is valuable for understanding the molecular properties of the azo dyes compounds and for synthesizing new ones in the future.

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Azo dyes with ESIPT core for textile applications and DFT study

Cited by 31 publications

References 20 publications

Ultra-fast excited-state dynamics of substituted trans-naphthalene azo moieties

Ultra-fast excited-state dynamics of substituted trans-naphthalene azo moieties

Excited-State Proton Transfer from Embedded Photoacids to Silanols on Mesostructured Surfaces: Role of Structural Heterogeneity

Synthesis, characterization, DFT, and TD-DFT studies of (E)-5-((4,6-dichloro-1,3,5-triazin-2-yl)amino)-4-hydroxy-3-(phenyldiazenyl)naphthalene-2,7-diylbis(hydrogen sulfite)

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