Red Emitting Monoazo Disperse Dyes with Phenyl(1H-benzoimidazol-5-yl) Methanone as Inbuilt Photostabilizing Unit: Synthesis, Spectroscopic, Dyeing and DFT Studies

  • Amol G. Jadhav
  • Suvidha S. Shinde
  • Nagaiyan Sekar
ORIGINAL ARTICLE
  • 29 Downloads

Abstract

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.

Keywords

Phenyl(1H-benzoimidazol-5-yl)methanone Fluorescent monoazo dyes Solvatochromism Aza-hydrazone and DFT study 

Notes

Acknowledgements

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).

Supplementary material

10895_2018_2226_MOESM1_ESM.docx (1.4 mb)
ESM 1 (DOCX 1442 kb)

References

  1. 1.
    Bhide R, Jadhav AG, Sekar N (2016) Light fast monoazo dyes with an inbuilt photostabilizing unit: Synthesis and computational studies. Fibers Polym 17:349–357.  https://doi.org/10.1007/s12221-016-5717-3 CrossRefGoogle Scholar
  2. 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. 3.
    Sekar N (2014) Natural colorants versus synthetic colorants. Colourage 61:54–56Google Scholar
  4. 4.
    Bafana A, Devi SSCT (2011) Azo dyes: past, present and the future. Environ Rev 19:350–370CrossRefGoogle Scholar
  5. 5.
    Seesuriyachan P, Takenaka S, Kuntiya A et al (2007) Metabolism of azo dyes by Lactobacillus casei TISTR 1500 and effects of various factors on decolorization. Water Res 41:985–992.  https://doi.org/10.1016/j.watres.2006.12.001 CrossRefPubMedGoogle Scholar
  6. 6.
    Al-Sheikh M, Medrasi HY, Usef Sadek K, Mekheimer RA (2014) Synthesis and Spectroscopic Properties of New Azo Dyes Derived from 3-Ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole. Molecules 19:2993–3003.  https://doi.org/10.3390/molecules19032993 CrossRefPubMedGoogle Scholar
  7. 7.
    Abdou MM (2013) Thiophene-Based Azo Dyes and Their Applications in Dyes. Chemistry 3:126–135.  https://doi.org/10.5923/j.chemistry.20130305.02. Google Scholar
  8. 8.
    Athalye A (2015) Automotive Textiles. Int J Text Eng Process 1:42–52Google Scholar
  9. 9.
    Ravve A (2006) Photosensitizers and Photoinitiators. In: Light React Synth Polym. Springer New York, New York, pp 23–122CrossRefGoogle Scholar
  10. 10.
    Jiang X, Rui Y, Chen G (2009) Improved Properties of Cotton by Atmospheric Pressure Plasma Polymerization Deposition of Sericin. J Vinyl Addit Technol 21:129–133.  https://doi.org/10.1002/vnl Google Scholar
  11. 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. 12.
    Bochet CG (2014) 9.13 Organic Photochemistry. In: Compr Org Synth II. Elsevier, pp 330–350Google Scholar
  13. 13.
    Jadhav AG, Shinde SS, Lanke SK, Sekar N (2017) Benzophenone based fluorophore for selective detection of Sn2+ ion: Experimental and theoretical study. Spectrochim Acta Part A Mol Biomol Spectrosc 174:291–296.  https://doi.org/10.1016/j.saa.2016.11.051 CrossRefGoogle Scholar
  14. 14.
    Dorman G, Prestwich GD (1994) Benzophenone Photophores in Biochemistry. Biochemistry 33:5661–5673.  https://doi.org/10.1021/bi00185a001 CrossRefPubMedGoogle Scholar
  15. 15.
    Sen GA, Paul K, Luxami V (2015) Ratiometric fluorescent chemosensor for fluoride ion based on inhibition of excited state intramolecular proton transfer. Spectrochim Acta, Part A Mol Biomol Spectrosc 138:67–72.  https://doi.org/10.1016/j.saa.2014.11.026 CrossRefGoogle Scholar
  16. 16.
    Sen GA, Paul K, Luxami V (2016) Benzimidazole based ratiometric chemosensor for detection of CN− and Cu2+ ions in protic/aqueous system: Elaboration as XOR logic operation. Inorganica Chim Acta 443:57–63.  https://doi.org/10.1016/j.ica.2015.11.024 CrossRefGoogle Scholar
  17. 17.
    Kiguchi M, Evans PD (1998) Photostabilisation of wood surfaces using a grafted benzophenone UV absorber. Polym Degrad Stab 61:33–45.  https://doi.org/10.1016/S0141-3910(97)00124-9 CrossRefGoogle Scholar
  18. 18.
    Chou P-T, Chen Y-C, Yu W-S et al (2001) Excited-State Intramolecular Proton Transfer in 10-Hydroxybenzo[h]quinoline. J Phys Chem A 105:1731–1740.  https://doi.org/10.1021/jp002942w CrossRefGoogle Scholar
  19. 19.
    Mitchell D, Lukeman M, Lehnherr D, Wan P (2005) Formal Intramolecular Photoredox Chemistry of Meta-Substituted Benzophenones. Org Lett 7:3387–3389.  https://doi.org/10.1021/ol051381u CrossRefPubMedGoogle Scholar
  20. 20.
    Beckett A, Porter G (1963) Primary photochemical processes in aromatic molecules. Part 10.-Photochemistry of substituted benzophenones. Trans Faraday Soc 59:2051.  https://doi.org/10.1039/tf9635902051 CrossRefGoogle Scholar
  21. 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
  22. 22.
    Tsatsaroni EG, Eleftheriadis IC (2004) UV-absorbers in the dyeing of polyester with disperse dyes. Dyes Pigments 61:141–147.  https://doi.org/10.1016/j.dyepig.2003.10.002 CrossRefGoogle Scholar
  23. 23.
    Barsotti F, Brigante M, Sarakha M et al (2015) Photochemical processes induced by the irradiation of 4-hydroxybenzophenone in different solvents. Photochem Photobiol Sci 14:2087–2096.  https://doi.org/10.1039/c5pp00214a CrossRefPubMedGoogle Scholar
  24. 24.
    Bhasikuttan a C, Singh a K, Palit DK et al (1998) Laser Flash Photolysis Studies on the Monohydroxy Derivatives of Benzophenone. Laser Flash Photolysis Studies on the Monohydroxy Derivatives of Benzophenone J Phys Chem 102:3470–3480.  https://doi.org/10.1021/jp972375l Google Scholar
  25. 25.
    Das PK, Encinas MV, Scaiano JC (1981) Laser flash photolysis study of the reactions of carbonyl triplets with phenols and photochemistry of p-hydroxypropiophenone. J Am Chem Soc 103:4154–4162.  https://doi.org/10.1021/ja00404a029 CrossRefGoogle Scholar
  26. 26.
    Palit DK (2005) Photophysics and excited state relaxation dynamics of p-hydroxy and p-amino-substituted benzophenones: a review. Res Chem Intermed 31:205–225.  https://doi.org/10.1163/1568567053147020 CrossRefGoogle Scholar
  27. 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
  28. 28.
    Kumar D, Justin Thomas KR, Lee C, Ho K (2014) Organic Dyes Containing Fluorene Decorated with Imidazole Units for Dye-Sensitized Solar Cells. J Org Chem 79:3159–3172.  https://doi.org/10.1021/jo500330r CrossRefPubMedGoogle Scholar
  29. 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. 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
  31. 31.
    Zhang X, Chen Y (2013) Synthesis and fluorescence of dicyanoisophorone derivatives. Dyes Pigments 99:531–536.  https://doi.org/10.1016/j.dyepig.2013.05.031 CrossRefGoogle Scholar
  32. 32.
    Li W, Lin W, Wang J, Guan X (2013) Phenanthro[9,10- d ]imidazole-quinoline Boron Difluoride Dyes with Solid-State Red Fluorescence. Org Lett 15:1768–1771.  https://doi.org/10.1021/ol400605x CrossRefPubMedGoogle Scholar
  33. 33.
    Prostota Y, Kachkovsky OD, Reis LV, Santos PF (2013) New unsymmetrical squaraine dyes derived from imidazo[1,5-a]pyridine. Dyes Pigments 96:554–562.  https://doi.org/10.1016/j.dyepig.2012.10.006 CrossRefGoogle Scholar
  34. 34.
    Fouassier J, Allonas X, Burget D (2003) Photopolymerization reactions under visible lights: principle, mechanisms and examples of applications. Prog Org Coatings 47:16–36.  https://doi.org/10.1016/S0300-9440(03)00011-0 CrossRefGoogle Scholar
  35. 35.
    Wan Z, Zhou L, Jia C et al (2014) Comparative study on photovoltaic properties of imidazole-based dyes containing varying electron acceptors in dye-sensitized solar cells. Synth Met 196:193–198.  https://doi.org/10.1016/j.synthmet.2014.08.005 CrossRefGoogle Scholar
  36. 36.
    Tsai M, Hsu Y-C, Lin JT et al (2007) Organic Dyes Containing 1 H -Phenanthro[9,10- d ]imidazole Conjugation for Solar Cells. J Phys Chem C 111:18785–18793.  https://doi.org/10.1021/jp075653h CrossRefGoogle Scholar
  37. 37.
    Shank NI, Zanotti KJ, Lanni F et al (2009) Enhanced Photostability of Genetically Encodable Fluoromodules Based on Fluorogenic Cyanine Dyes and a Promiscuous Protein Partner. J Am Chem Soc 131:12960–12969.  https://doi.org/10.1021/ja9016864 CrossRefPubMedPubMedCentralGoogle Scholar
  38. 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. 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. 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
  41. 41.
    Kano N, Yamamura M, Kawashima T (2015) 2,2′-Disilylazobenzenes Featuring Double Intramolecular Nitrogen⋯Silicon Coordination: A Photoisomerizable Fluorophore. Dalt Trans 44:16256–16265.  https://doi.org/10.1039/C5DT02038G CrossRefGoogle Scholar
  42. 42.
    Satam MA, Raut RK, Sekar N (2013) Fluorescent azo disperse dyes from 3-(1,3-benzothiazol-2-yl)naphthalen-2-ol and comparison with 2-naphthol analogs. Dyes Pigments 96:92–103.  https://doi.org/10.1016/j.dyepig.2012.07.019 CrossRefGoogle Scholar
  43. 43.
    Yoshino J, Kano N, Kawashima T (2013) Fluorescent azobenzenes and aromatic aldimines featuring an N–B interaction. Dalt Trans 42:15826.  https://doi.org/10.1039/c3dt51689j CrossRefGoogle Scholar
  44. 44.
    Deshmukh MS, Sekar N (2015) Chemiluminescence properties of isoluminol related mono azo disperse dyes: Experimental and DFT based approach to photophysical properties. Dyes Pigments 115:127–134.  https://doi.org/10.1016/j.dyepig.2014.12.019 CrossRefGoogle Scholar
  45. 45.
    Tathe AB, Sekar N (2016) Red Emitting Coumarin—Azo Dyes : Synthesis, Characterization, Linear and Non-linear Optical Properties-Experimental and Computational Approach. J Fluoresc 26:1279–1293.  https://doi.org/10.1007/s10895-016-1815-2 CrossRefPubMedGoogle Scholar
  46. 46.
    Warde U, Sekar N (2017) NLOphoric mono-azo dyes with negative solvatochromism and in-built ESIPT unit from ethyl 1,3-dihydroxy-2-naphthoate: Estimation of excited state dipole moment and pH study. Dyes Pigments 137:384–394.  https://doi.org/10.1016/j.dyepig.2016.10.032 CrossRefGoogle Scholar
  47. 47.
    Jadhav AG, Sekar N (2017) Substituent Modulation from ESIPT to ICT Emission in Benzoimidazolphenyl-methanones Derivatives: Synthesis, Photophysical and DFT Study. J Solut Chem 46:777–797.  https://doi.org/10.1007/s10953-017-0602-2 CrossRefGoogle Scholar
  48. 48.
    Frisch MJ, Trucks GW, Schlegel HB, et al (2009) Gaussian 09, Revision C.01. Gaussian 09, Revis B01, Gaussian, Inc, Wallingford CTGoogle Scholar
  49. 49.
    Becke AD (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 38:3098–3100.  https://doi.org/10.1103/PhysRevA.38.3098 CrossRefGoogle Scholar
  50. 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
  51. 51.
    Shaikh KA, Patil VA, Shaikh PA (2012) An Efficient and Convenient Synthesis of Imidazolines and Benzimidazoles via Oxidation of Carbon-Nitrogen Bond in Water Media. Chinese J Chem 30:924–928.  https://doi.org/10.1002/cjoc.201100210 CrossRefGoogle Scholar
  52. 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
  53. 53.
    Munro CH, Smith WE, Armstrong DR, White PC (1995) Assignments and Mechanism of SERRS of the Hydrazone Form for the Azo Dye Solvent Yellow 14. J Phys Chem 99:879–885.  https://doi.org/10.1021/j100003a008 CrossRefGoogle Scholar
  54. 54.
    Olson DH, Camblor MA, Villaescusa LA, Kuehl GH (2004) Light hydrocarbon sorption properties of pure silica Si-CHA and ITQ-3 and high silica ZSM-58. Microporous Mesoporous Mater 67:27–33.  https://doi.org/10.1016/j.micromeso.2003.09.025 CrossRefGoogle Scholar
  55. 55.
    Maximilian Paul Schmidt W-B, and Hermann Neuroth, Wiesbaden G (1934) LIGHT-SENSITIVE LAYER. 3–4.Google Scholar
  56. 56.
    Chen X-C, Tao T, Wang Y-G et al (2012) Azo-hydrazone tautomerism observed from UV-vis spectra by pH control and metal-ion complexation for two heterocyclic disperse yellow dyes. Dalt Trans 41:11107.  https://doi.org/10.1039/c2dt31102j CrossRefGoogle Scholar
  57. 57.
    Peters AT (1995) Freeman HS. Modern Colorants, Synthesis and Structure.  https://doi.org/10.1007/978-94-011-1356-4 Google Scholar
  58. 58.
    Lanke SK, Sekar N (2016) Aggregation induced emissive carbazole-based push pull NLOphores: Synthesis, photophysical properties and DFT studies. Dyes Pigments 124:82–92.  https://doi.org/10.1016/j.dyepig.2015.09.013 CrossRefGoogle Scholar
  59. 59.
    Leu WCW, Fritz AE, Digianantonio KM, Hartley CS (2012) Push-pull macrocycles: Donor-acceptor compounds with paired linearly conjugated or cross-conjugated pathways. J Org Chem 77:2285–2298.  https://doi.org/10.1021/jo2026004 CrossRefPubMedGoogle Scholar
  60. 60.
    Tathe AB, Sekar N (2016) Red-emitting NLOphoric carbazole-coumarin hybrids - Synthesis, photophysical properties and DFT studies. Dyes Pigments 129:174–185.  https://doi.org/10.1016/j.dyepig.2016.02.026 CrossRefGoogle Scholar
  61. 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
  62. 62.
    Parr RG, Szentpály LV, Liu S (1999) Electrophilicity index. J Am Chem Soc 121:1922–1924.  https://doi.org/10.1021/ja983494x CrossRefGoogle Scholar
  63. 63.
    Gupta VD, Tathe AB, Padalkar VS et al (2013) Red emitting solid state fluorescent triphenylamine dyes: Synthesis, photo-physical property and DFT study. Dyes Pigments 97:429–439.  https://doi.org/10.1016/j.dyepig.2012.12.024 CrossRefGoogle Scholar
  64. 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

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Amol G. Jadhav
    • 1
  • Suvidha S. Shinde
    • 1
  • Nagaiyan Sekar
    • 1
  1. 1.Department of Dyestuff TechnologyInstitute of Chemical TechnologyMumbaiIndia

Personalised recommendations