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Synthesis and Spectroscopic Properties of Carbazole-Oxadiazoles

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Abstract

Four new carbazole-oxadiazole derivatives (3a-b, 6a-b) were prepared from the reaction of aromatic aldehydes and carbohydrazides which were synthesized from carbazole aldehydes namely 9-hexyl-9H-carbazole-3-carbaldehyde 1 and 4-(9H-carbazole-9-yl)benzaldehyde 4 and acid hydrazides. The structures of the new derivatives were confirmed by 1H-NMR and FT-IR. The optical properties such as maximum absorption and emission wavelengths (λ; nm), molar extinction coefficients (ε; cm−1 M−1), Stoke’s shifts (ΔλST; nm) and quantum yields (ϕF), of the carbazole-oxadiazole derivatives were declared in dichloromethane, toluene and tetrahydrofuran solutions.

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References

  1. Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Burn PL, Holmes AB (1990) Light-emitting diodes based on conjugated polymers. Nature 347:539–541

    Article  CAS  Google Scholar 

  2. Tao XT, Zhang YD, Wada T, Sasabe H, Suzuki H, Watanabe T, Miyata S (1998) Hyperbranched polymers for electroluminescence applications. Adv Mater 10:226–230

    Article  CAS  Google Scholar 

  3. Rani V, Santhanam KSV (1998) Polycarbazole-based electrochemical transistor. J Solid State Electr 2:99–101

    Article  CAS  Google Scholar 

  4. Wada T, Zhang YD, Choi YS, Sasabe H (1993) Photoconductive crystals for nonlinear optics: molecular design and crystal structure. J Phys D Appl Phys 26:221–224

    Article  Google Scholar 

  5. Scott JC, Pautmeier LT, Moerner WE (1992) Photoconductivity studies of photorefractive polymers. J Opt Soc Am 9:2059–2064

    Article  CAS  Google Scholar 

  6. Zhang Y, Wang L, Wada T, Sasabe H (1996) A new synthetic approach for polymers containing a high density of second-order nonlinear optical chromophores. Chem Commun: 559–561

  7. Kuo WJ, Hsiue GH, Jeng RJ (2002) Synthesis and macroscopic second-order nonlinear optical properties of poly(ether imide)s containing a novel two-dimensional carbazole chromophore with nitro acceptors. J Mater Chem 12:868–878

    Article  CAS  Google Scholar 

  8. Ostraskaite J, Voska V, Antulis J, Gaidelis V, Jankauskas V, Grazulevicius JV (2002) High hole mobilities in carbazole-based glass-forming hydrazones. J Mater Chem 12:3469–3474

    Article  Google Scholar 

  9. Thomas KRJ, Lin JT, Tao YT, Ko CW (2001) Light-emitting carbazole derivatives: potential electroluminescent materials. J Am Chem Soc 123:9404–9411

    Article  CAS  PubMed  Google Scholar 

  10. Thomas KR J, Lin JT, Lin YY, Tsai C, Sun SS (2001) Self-assembly molecular architectures incorporating fluorene- and carbazole-based bichromic oligopyridines. Novel photoactive materials. Organometallics 20:2262–2269

    Article  CAS  Google Scholar 

  11. Thomas KRJ, Lin JT, Tao YT, Chuen CH (2002) Green and yellow electroluminescent dipolar carbazole derivatives: features and benefits of electron-withdrawing segments. Chem Mater 14:3852–3859

    Article  CAS  Google Scholar 

  12. Bai FL, Zheng M, Yu G, Zhu DB (2000) The photo-and electroluminescence of some novel light emitting copolymers. Thin Solid Films 363:118–121

    Article  CAS  Google Scholar 

  13. Romero DB, Schaer M, Leclerc M, Ades D, Siove A, Zuppiroli L (1996) The role of carbazole in organic light-emitting devices. Synth Met 80:271–277

    Article  CAS  Google Scholar 

  14. Mashraqui SH, Kenny RS, Ghadigaonkar SG, Krishnan A, Bhattacharya M, Das PK (2004) Synthesis and nonlinear optical properties of some donor-acceptor oxadiazoles. Opt Mater 27:257–260

    Article  CAS  Google Scholar 

  15. Chidirala S, Ulla H, Valaboju A, Kiran MR, Maneesha Esther Mohanty ME, Satyanarayan MN, Umesh G, Bhanuprakash K, Vaidya Jayathirtha Rao VJ (2015) Pyrene–oxadiazoles for organic light-emitting diodes: triplet to singlet energy transfer and role of hole-injection/hole-blocking materials. J Org Chem 81:603–614

    Article  PubMed  Google Scholar 

  16. Zhang C, Von Seggern H, Pakbaz K, Kraabel B, Schmidt HW, Heeger AJ (1994) Blue electroluminescent diode utilizing blends of Poly(phenylenevinylene) in Poly(9-vinylcarbazol). Synth Met 62:35–40

    Article  CAS  Google Scholar 

  17. Liu Y, Liu MS, Li XC, Jen AKY (1998) Synthesis and characterization of a novel light-emitting polymer containing highly efficient hole-transporting aromatic diamine. Chem Mater 10:3301–3304

    Article  CAS  Google Scholar 

  18. Hosokawa C, Kawasaki N, Sakamoto S, Kusumoto T (1992) Bright blue electroluminescence from hole transporting polycarbonate. Appl Phys Lett 61:2503–2505

    Article  CAS  Google Scholar 

  19. Wang H, Ryu J T, Han Y S, Kim D H, Choi B D, Kwon Y (2007) Synthesis and optical properties of copolymers containing carbazole and 1,3,4-Oxadiazole groups as blue host matrix and charge transport materials for polymer light emitting devices. Mol Cryst Liq Cryst 463: 285–295

    Article  CAS  Google Scholar 

  20. Jin Y, Kim JY, Park SH, Kim J, Lee S, Lee K, Suh H (2005) Syntheses and properties of electroluminescent polyfluorene-based conjugated polymers, containing oxadiazole and carbazole units as pendants, for LEDs. Polymer 46:12158–12165

    Article  CAS  Google Scholar 

  21. Jin Y, Song S, Kim JY, Kim H, Lee K, Suh H (2008) Synthesis and properties of polyfluorene, containing oxadiazole and carbazole units as pendants for white light-emitting diodes. Thin Solid Films 516:7373–7380

    Article  CAS  Google Scholar 

  22. Wang H, Ryu J T, Kwon Y, Han Y S (2009) Synthesis and properties of random carbazole/1,3,4-oxadiazole/aniline copolymers for organic light-emitting devices. Mol Cryst Liq Cryst 499: 370–379

    CAS  Google Scholar 

  23. Ku CH, Kuo CH, Leung MK, Hsieh KH (2009) Carbazole–oxadiazole containing polyurethanes as phosphorescent host for organic light emitting diodes. Eur Polym J 45:1545–1553

    Article  CAS  Google Scholar 

  24. Peng Q, Xu J, Li M, Zheng W (2009) Blue emitting polyfluorenes containing dendronized carbazole and oxadiazole pendants: synthesis, optical properties, and electroluminescent properties. Macromolecules 42:5478–5485

    Article  CAS  Google Scholar 

  25. Nam Y, Matsuura Y, Kinoshita M, Ikeda T (2009) Phosphorescent PLEDs using donor-acceptor liquid-crystalline polymers containing oxadiazole and carbazole. Mol Cryst Liq Cryst 513(1):142–152

    Article  CAS  Google Scholar 

  26. Shin MH, Wong FF, Lin CM, Chen WY, Yeh MY (2006) New synthesis of highly potential efficient bluish-green electroluminescent materials based on 1,3,4-oxadiazole-triazolopyridinone-carbazole derivatives for single-layer devices. Heteroat Chem 17:160–165

    Article  CAS  Google Scholar 

  27. Dıaz JL, Villacampa B, Lopez-Calahorra F, Velasco D (2002) Experimental and theoretical study of a new class of acceptor group in chromophores for nonlinear optics:2-substituted 4-methylene-4H-oxazol-5-ones. Chem Mater 14: 2240–2251

    Article  Google Scholar 

  28. Shao H, Chen X, Wang Z, Lu P (2007) Synthesis and fluorescence properties of carbazole and fluorene-based compounds. J Lumin 127:349–354

    Article  CAS  Google Scholar 

  29. Gundogdu C, Topkaya D, Ozturk G, Alp S, Ergun Y (2010) Synthesis of novel carbazolyl-oxazolone derivatives and their spectroscopic properties. J Heterocycl Chem 47:1450–1453

    Article  CAS  Google Scholar 

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Correspondence to Mustafa Yavuz Ergün.

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Gündoğdu, L., Şen, N., Hızlıateş, C.G. et al. Synthesis and Spectroscopic Properties of Carbazole-Oxadiazoles. J Fluoresc 27, 2095–2100 (2017). https://doi.org/10.1007/s10895-017-2147-6

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  • DOI: https://doi.org/10.1007/s10895-017-2147-6

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