Skip to main content
Log in

Synthesis and polymerization of 1,5-bis(N-carbazolyl)pentane with its structural and behavioral highlights

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

Carbazole, the well-known electron donor and hole-transporting organic light-emitting molecule was modified into 1,5-bis[N-carbazolyl]pentane (1,5-BNCP) by introducing the saturated pentane spacer. Such insertion fixed the certain space between growing polymer chains and demonstrated π–π stacking effect over its morphology and structure. Its contribution in improving the thermal stability and photosensitization was also investigated. The FT-IR and 1H NMR was used to characterize monomer. Morphology of subsequently polymerized material was seen under SEM. The position of polymerization and structural change were studied by FT-IR and XRD, respectively. Thermal study with reference to glass transition temperature and stability was analyzed by DSC and TGA. Optical properties of monomer and polymer were investigated by UV–visible and photoluminescent spectrophotometer. The material was found crystalline, thermally stable, highly photosensitized and white light emitter.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Chen Y, Yamamura T, Igarashi K (2000) Photosensitization of carbazole derivatives in cationic polymerization with a novel sensitivity to near-UV light. J Polym Sci Part A Polym Chem 38(1):90–100

    Article  CAS  Google Scholar 

  2. Higginbotham H, Karon K, Ledwon P, Data P (2017) Carbazoles in optoelectronic applications. Display Imaging 2:207–216

    Google Scholar 

  3. Grigalevicius S, Zhang B, Xie Z, Forster M, Scherf U (2011) Polycarbazole-based networks made by photo-crosslinking for hole transporting layers of OLED devices. Org Electron 12(12):2253–2257

    Article  CAS  Google Scholar 

  4. Yoon KR, Ko S-O, Lee SM, Lee H (2007) Synthesis and characterization of carbazole derived nonlinear optical dyes. Dyes Pigments 75(3):567–573

    Article  CAS  Google Scholar 

  5. Wang Z-S, Koumura N, Cui Y, Takahashi M, Sekiguchi H, Mori A, Kubo T, Furube A, Hara K (2008) Hexylthiophene-functionalized carbazole dyes for efficient molecular photovoltaics: tuning of solar-cell performance by structural modification. Chem Mater 20(12):3993–4003

    Article  CAS  Google Scholar 

  6. Boudreault P-LT, Beaupré S, Leclerc M (2010) Polycarbazoles for plastic electronics. Polym Chem 1(2):127–136

    Article  CAS  Google Scholar 

  7. Gaudiana R, Brabec C (2008) Organic materials: fantastic plastic. Nat Photonics 2(5):287–289

    Article  CAS  Google Scholar 

  8. Atahan-Evrenk Ş, Aspuru-Guzik A (2014) Prediction and Theoretical characterization of p-type organic semiconductor crystals for field-effect transistor applications. In: Prediction and calculation of crystal structures. Springer, pp 95–138

  9. Ahmad Z, Choudhary M, Mirza M, Mirza J (2016) Synthesis and characterization of Ag@ polycarbazole nanoparticles using different oxidants and their dispersion behavior. Mater Sci Poland 34(1):79–84

    Article  CAS  Google Scholar 

  10. Larrubia MA, Gutièrrez-Alejandre Ad, Ramı̀rez J, Busca G (2002) A FT-IR study of the adsorption of indole, carbazole, benzothiophene, dibenzothiophene and 4,6-dibenzothiophene over solid adsorbents and catalysts. Appl Catal A 224(1):167–178

    Article  CAS  Google Scholar 

  11. Zahoor A, Qiu T, Zhang J, Li X (2009) Synthesis and characterization of Ag@ polycarbazole nanoparticles and their novel optical behavior. J Mater Sci 44(22):6054–6059

    Article  CAS  Google Scholar 

  12. Ahmad Z, Choudhary MA, Mehmood A, Wakeel R, Akhtar T, Rafiq MA (2016) Synthesis of polypyrrole nano/microspheres using cobalt(III) as an oxidizing agent and its ammonia sensing behavior. Macromol Res 24(7):596–601

    Article  CAS  Google Scholar 

  13. Miyazaki T, Kim S-K, Hoshino K (2006) Nanostructured hybrid materials formed by cell reaction between polycarbazole and metals. Chem Mater 18(22):5302–5311

    Article  CAS  Google Scholar 

  14. Siove A, Ades D (2004) Synthesis by oxidative polymerization with FeCl3 of a fully aromatic twisted poly(3, 6-carbazole) with a blue-violet luminescence. Polymer 45(12):4045–4049

    Article  CAS  Google Scholar 

  15. Lei W, Wu Q, Si W, Gu Z, Zhang Y, Deng J, Hao Q (2013) Electrochemical determination of imidacloprid using poly (carbazole)/chemically reduced graphene oxide modified glassy carbon electrode. Sens Actuators B Chem 183:102–109

    Article  CAS  Google Scholar 

  16. Pokhrel B, Kalita A, Dolui S (2011) Synthesis, characterization, and study of electrochemical behavior of N-alkyl substituted polycarbazole derivatives. Int J Polym Mater 60(11):825–836

    Article  CAS  Google Scholar 

  17. Ustamehmetoğlu B, Akar A, Kizilcan N, Kelleboz E (2012) Copolymers of carbazoles and methyl ethyl ketone formaldehyde resin. Pigment Resin Technol 41(1):25–33

    Article  Google Scholar 

  18. Dong W, Fei T, Palma-Cando A, Scherf U (2014) Aggregation induced emission and amplified explosive detection of tetraphenylethylene-substituted polycarbazoles. Polym Chem 5(13):4048–4053

    Article  CAS  Google Scholar 

  19. Kushida S, Okabe S, Dao TD, Ishii S, Nagao T, Saeki A, Kijima M, Yamamoto Y (2016) Self-assembled polycarbazole microspheres as single-component, white-colour resonant photoemitters. RSC Adv 6(58):52854–52857

    Article  CAS  Google Scholar 

  20. Srivastava A, Chakrabarti P (2017) Experimental characterization of electrochemically polymerized polycarbazole film and study of its behavior with different metals contacts. Appl Phys A 123(12):784

    Article  CAS  Google Scholar 

  21. Huyal IO, Koldemir U, Ozel T, Demir HV, Tuncel D (2008) On the origin of high quality white light emission from a hybrid organic/inorganic light emitting diode using azide functionalized polyfluorene. J Mater Chem 18(30):3568–3574

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The Higher Education Commission (HEC), Pakistan, and ORIC MUST are gratefully acknowledged for financial funding.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zahoor Ahmad.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ahmad, Z., Saeed, B., Akhtar, T. et al. Synthesis and polymerization of 1,5-bis(N-carbazolyl)pentane with its structural and behavioral highlights. Polym. Bull. 77, 1205–1216 (2020). https://doi.org/10.1007/s00289-019-02797-w

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-019-02797-w

Keywords

Navigation