Red Emitting Monoazo Disperse Dyes with Phenyl(1H-benzoimidazol-5-yl) Methanone as Inbuilt Photostabilizing Unit: Synthesis, Spectroscopic, Dyeing and DFT Studies
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Synthesis of three novel phenyl(1H-benzoimidazol-5-yl)methanone based fluorescent monoazo disperse dyes and their characterization by spectroscopic methods (1H NMR, 13C NMR, IR and MS) are presented. Insertion of phenyl(1H-benzoimidazol-5-yl)methanone moiety bring about induced fluorescence properties and enhanced photostability as compared to the previously reported analogues (CI Solvent Yellow 14, 4-diethylamino-2-hydroxy-1-diazobenzene and 7-(diethylamino)-4-hydroxy-3-(phenyldiazenyl)-2H-chromen-2-one). Synthesized phenyl(1H-benzoimidazol-5-yl)methanone based dyes exhibited red-shifted absorption maxima (497–516 nm), high molar extinction coefficients and are emitting in the far-red region (565–627 nm). Moreover, naphthalene-comprising dyes showed negative solvatochromism while N,N-diethylamine comprising dyes showed positive solvatochromism and are in good agreement with solvent polarity graphs and the computed energy levels of highest occupied and lowest unoccupied molecular orbitals. Synthesised dyes have better photostability (light fastness) and sublimation fastness on dyed polyester and nylon compared to reported analogues. DFT calculated energies, electrophilicity index and Frontier Molecular Orbitals (FMO’s) enabled to evaluate the stabilities of azo and hydrazone forms of the dyes.
KeywordsPhenyl(1H-benzoimidazol-5-yl)methanone Fluorescent monoazo dyes Solvatochromism Aza-hydrazone and DFT study
One of the author Amol G. Jadhav is thankful to UGC for financial assistance in terms of SRF.
Suvidha Shinde is thankful to the Centre of Advanced Studies (UGC) for JRF and SRF under the Special Assistance Programme (SAP).
- 2.Sharma RK, Gulati S, Pandey A, Adholeya A (2012) Novel, efficient and recyclable silica based organic–inorganic hybrid Nickel catalyst for degradation of dye pollutants in a newly designed chemical reactor. Appl Catal B Environ 125:247–258. https://doi.org/10.1016/j.apcatb.2012.05.046 CrossRefGoogle Scholar
- 3.Sekar N (2014) Natural colorants versus synthetic colorants. Colourage 61:54–56Google Scholar
- 8.Athalye A (2015) Automotive Textiles. Int J Text Eng Process 1:42–52Google Scholar
- 11.Patel HM (2014) Synthesis, Structure Investigation and Dyeing Assessment of Novel Bisazo Disperse Dyes Derived from UV Absorbing Material. IOSR. J Appl Chem 6:51–55Google Scholar
- 12.Bochet CG (2014) 9.13 Organic Photochemistry. In: Compr Org Synth II. Elsevier, pp 330–350Google Scholar
- 21.Dixit B, Patel H, Dixit R, Desai D (2010) Synthesis, characterization and dyeing assessment of novel acid azo dyes and mordent acid azo dyes based on 2- hydroxy-4-methoxybenzophenone on wool and silk fabrics. J Serbian Chem Soc 75:605–614. https://doi.org/10.2298/JSC090704039D CrossRefGoogle Scholar
- 27.Barsotti F, Ghigo G, Berto S, Vione D (2017) The nature of the light absorption and emission transitions of 4-hydroxybenzophenone in different solvents. A combined computational and experimental study. Photochem Photobiol Sci. https://doi.org/10.1039/C6PP00272B
- 29.Aulakh RK, Sandhu S, Tanvi, et al (2015) Designing and synthesis of imidazole based hole transporting material for solid state dye sensitized solar cells. Synth Met 205:92–97. doi: https://doi.org/10.1016/j.synthmet.2015.03.030
- 30.Skonieczny K, Ciuciu AI, Nichols EM et al (2012) Bright, emission tunable fluorescent dyes based on imidazole and π-expanded imidazole. J Mater Chem. https://doi.org/10.1039/c2jm33891b
- 38.Bamfield P, Britain) RS of C (Great (2001) Chapter 3. Phenomena Involving Absorption of Energy Followed by Emission of Light. In: Chromic Phenom. Royal Society of Chemistry, Cambridge, pp 234–365Google Scholar
- 39.Szuster L, Kaźmierska M, Król I (2004) Fluorescent dyes destined for dyeing high-visibility polyester textile products. Fibres Text East Eur 12:70–75Google Scholar
- 40.Youssef BM, Ahmed MHM, Arief MMH, Mashaly HM (2014) Synthesis and Application of Functional (Anti-UV) Azo-dyes based on γ -acid on Wool Fabrics. Indian J Sci Technol 7:1005–1013Google Scholar
- 48.Frisch MJ, Trucks GW, Schlegel HB, et al (2009) Gaussian 09, Revision C.01. Gaussian 09, Revis B01, Gaussian, Inc, Wallingford CTGoogle Scholar
- 50.Zhao Y, Truhlar DG (2008) The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other function. Theor Chem Accounts 120:215–241. https://doi.org/10.1007/s00214-007-0310-x CrossRefGoogle Scholar
- 52.Devi TC, Krishnan R, Kunju AS (2004) Synthesis and Characterization of Copper(II), Cobalt(II) and Manganese(II) Complexes of 2-(2′-hydroxynaphthylazo)-5-benzoulbenzimidazole. Asian J Chem 16:1611–1617Google Scholar
- 55.Maximilian Paul Schmidt W-B, and Hermann Neuroth, Wiesbaden G (1934) LIGHT-SENSITIVE LAYER. 3–4.Google Scholar
- 61.Mashaly HM, Abdelghaffar RA, Kamel MM, Youssef BM (2014) Dyeing of Polyester Fabric using Nano Disperse Dyes and Improving their Light Fastness using ZnO Nano Powder. Indian J Sci Technol 7:960–967Google Scholar
- 64.Hamdaoui M, Lanouar A, Halaoua S (2015) Study of Fluorescent Dyeing Process and Influence of Mixture Dyes on High-visibility. J Eng Fiber Fabr 10:89–96Google Scholar