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Unsymmetrical pyrazole-based new semiconductor oligomer: synthesis and optical properties

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Abstract

Poly(p-phenylene-1-(2,5-dimethylphenyl)-5-phenyl-1H-pyrazole-3,4-dicarboxy amide) (poly(PDPPD)) was synthesized from reactions of p-phenylene-diamine and 1-(2,5-dimethylphenyl)-5-phenyl-1H-pyrazole-3,4-dicarbonyl dichloride (monomer) by heating under solvent. This newly synthesized poly(PDPPD) was characterized by 1H, 13C-NMR, FT-IR, gel permeation chromatography (GPC). In addition, we investigated optical properties of the poly(PDPPD) containing the substituted pyrazole ring at different molarities. The average transmittance (T avg) values of the poly(PDPPD) in the visible (V) region were higher than the T avg values in the near-ultraviolet (NU) region. The T avg values of the poly(PDPPD) in the NU and visible (V) region decreased with increasing molarity. The absorption band edge (Absbe) value of the poly(PDPPD) decreased with increasing molarity. It was observed that the optical band gap (E g) of the poly(PDPPD) value decreased more with increasing molarity. The refractive index of the poly(PDPPD) decreased with increasing wavelength and decreasing molarity. The structure of the poly(PDPPD) in the lowest energy was optimized by DFT calculation and its HOMO–LUMO orbitals were plotted.

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References

  1. Kamal A, Shaik AB, Jain N, Kishor C, Nagabhushana A, Supriya B, Chourasiya SS, Suresh Y, Mishra KR, Addlaganatta A (2015) Design and synthesis of pyrazole–oxindole conjugates targeting tubulin polymerization as new anticancer agents. Eur J Med Chem 92:501–513

    Article  CAS  Google Scholar 

  2. Kendre BV, Landge MG, Jadhav WN, Bhusare SR (2013) Synthesis and bioactivities of some new 1H-pyrazole derivatives containing an aryl sulfonate moiety. Chin Chem Lett 24:325–328

    Article  CAS  Google Scholar 

  3. Mert S, Kasımoğulları R, Iça T, Çolak F, Altun A, Ok S (2014) Synthesis, structure–activity relationships, and in vitro antibacterial and antifungal activity evaluations of novel pyrazole carboxylic and dicarboxylic acid derivatives. Eur J Med Chem 78:86–96

    Article  CAS  Google Scholar 

  4. El-Sayed AAM, Abdel-Aziz IN, Abdel-Aziz MAA, El-Azab SA, ElTahir EHK (2012) Synthesis, biological evaluation and molecular modelling study of pyrazole and pyrazoline derivatives as selective COX-2 inhibitors and anti-inflammatory agents. Part 2. Bioorg Med Chem 20:3306–3316

    Article  CAS  Google Scholar 

  5. Shen SL, Zhu J, Li M, Zhao BX, Miao JY (2012) Synthesis of ferrocenyl pyrazole-containing chiral aminoethanol derivatives and their inhibition against A549 and H322 lung cancer cells. Eur J Med Chem 54:287–294

    Article  CAS  Google Scholar 

  6. Chambers LJ, Stevens AJ, Moses AP, Michel AD, Walter SD, Davies DJ, Livermore DG, Fonfria E, Demont EH, Vimal M, Theobald PJ, Beswick PJ, Gleave RJ, Roman SA, Stefan S (2010) Synthesis and structure–activity relationships of a series of (1H-pyrazol-4-yl) acetamide antagonists of the P2X7 receptor. Bioorg Med Chem Lett 20:3161–3164

    Article  CAS  Google Scholar 

  7. Kaya E, Gündüz B, Çetin A (2016) Synthesis and characterization of conjugated polymers containing phenyl and bithiophene: controlling of optical properties with molarity. Colloid Polym Sci 294:339–345

    Article  CAS  Google Scholar 

  8. Chang EM, Lee CT, Chen CY, Wong FF, Yeh MY (2008) Synthesis, optical properties, and characterization of new soluble conjugated poly (p-phenylenevinylene) derivatives constituted of alternating pyrazole and 1, 3, 4-oxadiazole moieties. Aust J Chem 61:342–349

    Article  CAS  Google Scholar 

  9. Lv HS, Zhao BX, Li JK, Xia Y, Lian S, Liu WY, Gong ZL (2010) The synthesis, characterization and optical properties of novel, substituted, pyrazoly1,3,4-oxadiazole derivatives. Dyes Pigments 86:25–31

    Article  CAS  Google Scholar 

  10. Bailey DM, Hansen PE, Hlavac AG, Baizman ER, Pear J, DeFelice AF, Feigensonf ME (1985) 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants. J Med Chem 28:256–260

    Article  CAS  Google Scholar 

  11. Siddall TL, Ouse DG, Benko ZL, Garvin GM, Jackson JL, McQuiston JM, Ricks MJ, Thibault TD, Turner JA, VanHeertum JC, Weimer MR (2002) Synthesis and herbicidal activity of phenyl-substituted benzoylpyrazoles. Pest Manag Sci 58:1175–1186

    Article  CAS  Google Scholar 

  12. Tahermansouri H, Biazar E (2013) Functionalization of carboxylated multi-wall carbon nanotubes with 3,5-diphenyl pyrazole and an investigation of their toxicity. New Carbon Mater 28:199–207

    Article  CAS  Google Scholar 

  13. Terrett NK, Bell AS, Brown D, Ellis P (1996) Sildenafil (Viagra TM), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction. Bioorg Med Chem Lett 6:1819–1824

    Article  Google Scholar 

  14. Ramkumar V, Kannan P (2015) Novel heterocyclic based blue and green emissive materials for opto-electronics. Opt Mater 46:314–323

    Article  CAS  Google Scholar 

  15. Oh CS, Lee JY (2014) High efficiency blue phosphorescent organic light-emitting diodes using 2-(1H-pyrazol-1-yl) pyridin-3-ol ligand based Be compound. Dyes Pigments 101:25–29

    Article  CAS  Google Scholar 

  16. Cherpak V, Stakhira P, Khomyak S, Volynyuk D, Hotra Z, Voznyak L, Oliynyk O (2011) Properties of 2, 6-di-tert-butyl-4-(2, 5-diphenyl-3, 4-dihydro-2H-pyrazol-3-yl)-phenol as hole-transport material for life extension of organic light emitting diodes. Opt Mater 33:1727–1731

    Article  CAS  Google Scholar 

  17. Duan Z, Hu D, Ohuchi H, Zhao M, Zhao G, Nishioka Y (2012) Organic field-effect transistors based on two phenylene–thiophene oligomer derivatives with a biphenyl or fluorene core. Synth Metals 162:1292–1298

    Article  CAS  Google Scholar 

  18. Back JY, Kim Y, An TK, Kang MS, Kwon SK, Park CE, Kim YH (2015) Synthesis and electrical properties of novel oligomer semiconductors for organic field-effect transistors (OFETs): asymmetrically end-capped acene-heteroacene conjugated oligomers. Dyes Pigments 112:220–226

    Article  CAS  Google Scholar 

  19. Kandasamy K, Ganesabaskaran S, Pachamuthu MP, Ramanathan AA (2015) A novel pyrazole biscoumarin based chemosensors for the selective detection of Cu2+ and Zn2+ ions. Spectrochim Acta A 148:184–188

    Article  CAS  Google Scholar 

  20. Sengupta S, Goswami A, Mondal R (2014) Silver-promoted gelation studies of an unorthodox chelating tripodal pyridine–pyrazole-based ligand: templated growth of catalytic silver nanoparticles, gas and dye adsorption. New J Chem 38:2470–2479

    Article  CAS  Google Scholar 

  21. Gondek E (2013) Photovoltaic solar cells based on pyrazole derivative. Mater Lett 112:94–96

    Article  CAS  Google Scholar 

  22. Gómez-Iglesias P, Guyon F, Khatyr A, Ulrich G, Knorr M, Martín-Alvarez JM, Villafañe F (2015) Luminescent rhenium (I) tricarbonyl complexes with pyrazolylamidino ligands: photophysical, electrochemical, and computational studies. Dalton Trans 44:17516–17528

    Article  Google Scholar 

  23. Ma CQ, Zhang LQ, Zhou JH, Wang XS, Zhang BW, Cao Y, Qiu Y (2002) 1,3-Diphenyl-5-(9-phenanthryl)-4, 5-dihydro-1H-pyrazole (DPPhP): structure, properties, and application in organic light-emitting diodes. J Mater Chem 12:3481–3486

    Article  CAS  Google Scholar 

  24. Deng L, Li J, Li W (2014) Solution-processible small-molecular host materials for high-performance phosphorescent organic light-emitting diodes. Dyes Pigments 102:150–158

    Article  CAS  Google Scholar 

  25. Singh M, Haverinen HM, Dhagat P, Jabbour GE (2010) Inkjet printing—process and its applications. Adv Mater 22:673–685

    Article  CAS  Google Scholar 

  26. Sakthinathan SP, Vanangamudi G, Thirunarayanan G (2012) Synthesis, spectral studies and antimicrobial activities of some 2-naphthyl pyrazoline derivatives. Spectrochim Acta A 95:693–700

    Article  CAS  Google Scholar 

  27. Yakimansky AV, Menshikova AY, Shevchenko NN, Shabsels BM, Bazhenova AG, Sel’kin AV, Alfimov MV (2009) From polymeric nanoparticles to dye-containing photonic crystals: synthesis, self-assembling, optical features, and possible applications. Polym Adv Tech 20:581–588

    Article  CAS  Google Scholar 

  28. Lan L, Zhang G, Dong Y, Ying L, Huang F, Cao Y (2015) Novel medium band gap conjugated polymers based on naphtho [1, 2-c: 5, 6-c] bis [1–3] triazole for polymer solar cells. Polymer 67:40–46

    Article  CAS  Google Scholar 

  29. Çetin A, Bildirici İ (2016) A study on synthesis and antimicrobial activity of 4-acyl-pyrazoles. J Saudi Chem Soc. doi:10.1016/j.jscs.2016.05.008

  30. Sener A, Tozlu I, Genc H, Bildirici I, Arisoy K (2007) Synthesis and some reactions of 4-(ethoxycarbonyl)-1,5-diphenyl-1H-pyrazole-3-carboxylic acid. J Het Chem 44:1077–1081

    Article  CAS  Google Scholar 

  31. Valero R, Gomes JR, Truhlar DG, Illas F (2010) Density functional study of CO and NO adsorption on Ni-doped MgO (100). J Chem Phys 132:104701–104709

    Article  Google Scholar 

  32. Raczynska E, Hallmann M, Duczmal K (2011) Quantum-chemical studies of amide–iminol tautomerism for inhibitor of lactate dehydrogenase: oxamic acid. Comput Theor Chem 964:310–317

    Article  CAS  Google Scholar 

  33. Tauc J, Menth A (1972) States in the gap. J Non-Crystal Solids 10:569–585

    Article  Google Scholar 

  34. Gündüz B (2015) Optical properties of poly [2-methoxy-5-(3′,7′-dimethyloctyloxy)-1,4-phenylenevinylene] light-emitting polymer solutions: effects of molarities and solvents. Polym Bull 72:3241–3267

    Article  Google Scholar 

  35. Gündüz B (2015) Surface morphology properties of the 5,5′-Di (4-biphenylyl)-2,2′-bithiophene (PPTTPP) nanofiber film and calculations of the optical parameters of the PPTTPP nanofiber optoelectronic devices. J Nanoelectron Optoelectron 10:1–8

    Article  Google Scholar 

  36. Ho WF, Uddin MA, Chan HP (2009) The stability of high refractive index polymer materials for high-density planar optical circuits. Polym Degrad Stab 94:158–161

    Article  CAS  Google Scholar 

  37. Ticha H, Tichy L (2002) Semiempirical relation between non-linear susceptibility (refractive index), linear refractive index and optical gap and its application to amorphous chalcogenides. J Optoelectron Adv Mater 4:381–386

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Sciences, Faculty of Education, Muş Alparslan University, Muş, Turkey

    Adnan Cetin & Bayram Gündüz

  2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yüzüncü Yıl University, Van, Turkey

    Nurettin Menges & Ishak Bildirici

Authors
  1. Adnan Cetin
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  2. Bayram Gündüz
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  4. Ishak Bildirici
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Correspondence to Adnan Cetin.

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Cetin, A., Gündüz, B., Menges, N. et al. Unsymmetrical pyrazole-based new semiconductor oligomer: synthesis and optical properties. Polym. Bull. 74, 2593–2604 (2017). https://doi.org/10.1007/s00289-016-1846-5

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  • DOI: https://doi.org/10.1007/s00289-016-1846-5

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