Skip to main content
SpringerLink
Log in

3,4-Dinitrothiophene as a central unit of quadrupolar push-pull-push systems

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

3,4-Dinitrothiophene has been utilized as a central acceptor unit in quadrupolar D-π-A-π-D push-pull-push chromophores. Employing cross-coupling and Knoevenagel reactions, nine novel chromophores bearing terminal methoxythiophene donor and systematically extended/varied π-linker were synthesized. Optical properties were studied by electronic absorption spectra. Fundamental optoelectronic properties were investigated by semiempirical PM7 calculations. It was shown that by varying the π-conjugated system the longestwavelength absorption maxima can be shifted from 341 to 489 nm. The calculated HOMO–LUMO gaps were found within the range of 6.69–7.29 eV, while the second-order molecular polarizabilities can be tuned from 0.038 to 1.578 × 10–27 esu.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Figure 1

Similar content being viewed by others

References

  1. Kawamoto, H. Proc IEEE 2002, 90, 460.

    Article  CAS  Google Scholar 

  2. (a) Sasabe, H.; Kido, J. Eur. J. Org. Chem. 2013, 7653. (b) Baeg, K.-J.; Binda, M.; Natali, D.; Caironi, M.; Noh, Y.-Y. Adv. Mater. 2013, 25, 4267. (c) Mukherjee, S.; Thilagar, P. Dyes Pigm. 2014, 110, 2. (d) Suzuki, M.; Aotake, T.; Yamaguchi, Y.; Noguchi, N.; Nakano, H.; Nakayama, K.; Yamada, H. J. Photochem. Photobiol., C. 2014, 18, 50. (e) Espíldora, E.; Delgado, J. L.; Martín, N. Isr. J. Chem. 2014, 54, 429. (f) Kanibolotsky, A. L.; Findlay, N. J.; Skabara, P. J. Beilstein J. Org. Chem. 2015, 11, 1749. (g) Gao, X.; Zhao, Z. Sci. China: Chem. 2015, 58, 947. (h) Fuse, S.; Takahashi, R.; Maitani, M. M.; Wada, Y.; Kaiho, T.; Tanaka, H.; Takahashi, T. Eur. J. Org. Chem. 2016, 508. (i) Gsänger, M.; Bialas, D.; Huang, L.; Stolte, M.; Würthner, F. Adv. Mater. 2016, 28, 3615. (j) Kaewpuang, T.; Prachumrak, N.; Namuangruk, S.; Jungsuttiwong, S.; Sudyoadsuk, T.; Pattanasattayavong, P.; Promarak, V. Eur. J. Org. Chem. 2016, 2528.

  3. Bureš, F. RSC Adv. 2014, 4, 58826.

  4. (a) Gauthier, S.; Vologdin, N.; Achelle, S.; Barsella, A.; Caro, B.; Robin-le Guen, F. Tetrahedron 2013, 69, 8392. (b) Kulhánek, J.; Bureš, F.; Pytela, O.; Pippig, F.; Danko, M.; Mikysek, T.; Padělková, Z.; Ludwig, M. J. Fluorine Chem. 2014, 161, 15. (c) Janiga, A.; Bednarska, D.; Thorsted, B.; Brewerb, J.; Gryko, D. T. Org. Biomol. Chem. 2014, 12, 2874. (d) Hrobárik, P.; Hrobáriková, V.; Semak, V.; Kasák, P.; Rakovský, E.; Polyzos, I.; Fakis, M.; Persephonis, P. Org. Lett. 2014, 16, 6358.

  5. (a) Zou, L.; Liu, Z.; Yan, X.; Liu, Y.; Fu, Y.; Liu, J.; Huang, Z.; Chen, X.; Qin, J. Eur. J. Org. Chem. 2009, 5587. (b) Huang, H.-F.; Xu, S.-H.; He, Y.-B.; Zhu, C.-C.; Fan, H.-L.; Zhou, X.-H.; Gao, X.-C.; Dai, Y.-F. Dyes Pigm. 2013, 96, 705. (c) Cvejn, D.; Michail, E.; Polyzos, I.; Almonasy, N.; Pytela, O.; Klikar, M.; Mikysek, T.; Giannetas, V.; Fakis, M.; Bureš, F. J. Mater. Chem. C. 2015, 3, 7345.

  6. Klikar, M.; Solanke, P.; Tydlitát, J.; Bureš, F. Chem. Rec. 2016, 16, 1886.

    Article  CAS  Google Scholar 

  7. Handbook of Thiophene-based Materials, Applications in Organic Electronics and Photonics; Perepichka, I. F.; Perepichka, D. F., Eds.; Wiley: Chichester, 2009, Vols. 1 and 2.

  8. (a) Yasuda, T.; Imase, T.; Nakamura, Y.; Yamamoto, T. Macromolecules 2005, 38, 4687. (b) Fasfous, I. I.; El-Abadelah, M. M.; Sabri, S. S. Lett. Org. Chem. 2011, 8, 712. (c) Speck, J. M.; Korb, M.; Schade, A.; Spange, S.; Lang, H. Organometallics 2015, 34, 3788.

  9. (a) Barlow, S.; Zhang, Q.; Kaafarani, B. R.; Risko, C.; Amy, F.; Chan, C. K.; Domercq, B.; Starikova, Z. A.; Antipin, M. Yu.; Timofeeva, T. V.; Kippelen, B.; Brédas, J. L.; Kahn, A.; Marder, S. R. Chem.–Eur. J. 2007, 13, 3537. (b) Karsten, B. P.; Janssen, R. A. J. Org. Lett. 2008, 10, 3513. (c) Li, Q.; Li, J.; Yang, R.; Deng, L.; Gao, Z.; Liu, D. Dyes Pigm. 2011, 92, 674. (d) Luo, M.; Wang, Q.; Wang, Z. Y. Org. Lett. 2011, 13, 4092. (e) Abdo, N. I.; El-Shehawy, A. A.; El-Barbary, A.-A.; Lee, J.-S. Eur. J. Org. Chem. 2012, 5540. (f) Xiao, Z.; Ye, G.; Liu, Y.; Chen, S.; Peng, Q.; Zuo, Q.; Ding, L. Angew. Chem., Int. Ed. 2012, 51, 9038. (g) Wang, Z.; Gao, Z.; Feng, Y.; Liu, Y.; Yang, B.; Liu, D.; Lv, Y.; Lu, P.; Ma, Y. Polymer 2013, 54, 6191. (h) Lu, X.; Fan, S.; Wu, J.; Jia, X.; Wang, Z.-S.; Zhou, G. J. Org. Chem. 2014, 79, 6480. (i) Qi, J.; Ni, L.; Yang, D.; Zhou, X.; Qiao, W.; Li, M.; Ma, D.; Wang, Z. Y. J. Mater. Chem. C 2014, 2, 2431.

  10. Kulhánek, J.; Bureš, F.; Opršal, J.; Kuznik, W.; Mikysek, T.; Růžička, A. Asian J. Org. Chem. 2013, 2, 422.

    Article  Google Scholar 

  11. Kulhánek, J.; Bureš, F.; Pytela, O.; Mikysek, T.; Ludvík, J.; Růžička, A. Dyes Pigm. 2010, 85, 57.

    Article  Google Scholar 

  12. Thompson, M. ArgusLab, Version 4.01; Planaria Software LC. http://www.arguslab.com

  13. Stewart, J. J. P. MOPAC2016, Version 16.093W; Stewart Computational Cheistry. http://OpenMOPAC.net

  14. (a) Klikar, M.; Bureš, F.; Pytela, O.; Mikysek, T.; Padělková, Z.; Barsella, A.; Dorkenoo, K.; Achelle, S. New J. Chem. 2013, 37, 4230. (b) Bureš, F.; Pytela, O.; Diederich, F. J. Phys. Org. Chem. 2009, 22, 155. (c) Bureš, F.; Pytela, O.; Kivala, M.; Diederich, F. J. Phys. Org. Chem. 2011, 24, 274.

  15. (a) Řezáč, J.; Hobza, P. J. Chem. Theory Comput. 2012, 8, 141. (b) Maia, J. D. C.; Carvalho, G. A. U.; Mangueira, C. P.; Santana, S. R.; Cabral, L. A. F.; Rocha, G. B. J. Chem. Theory Comput. 2012, 8, 3072.

  16. Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; John Wiley & Sons: New York, 1991.

    Google Scholar 

  17. Manecke, G.; Härtel, M. Chem. Ber. 1973, 106, 655.

    Article  CAS  Google Scholar 

  18. Miyaura N.; Ishiyama T. Eur. Patent 1481978A1.

  19. Batista, R. M. F.; Costa, S. P. G.; Belsley, M.; Lodeiro, C.; Raposo, M. M. M. Tetrahedron 2008, 64, 9230.

    Article  CAS  Google Scholar 

  20. Rodríguez, J. G.; Martín-Villamil, R.; Lafuente, A. Tetrahedron 2003, 59, 1021.

    Article  Google Scholar 

  21. Meier, H.; Mühling, B.; Oehlhof, A.; Theisinger, S.; Kirsten, E. Eur. J. Org. Chem. 2006, 405.

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 53210, Czech Republic

    Jiří Kulhánek, Miroslav Ludwig, Filip Bureš & Jiří Tydlitát

Authors
  1. Jiří Kulhánek
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Miroslav Ludwig
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Filip Bureš
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jiří Tydlitát
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jiří Tydlitát.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(1), 42–45

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kulhánek, J., Ludwig, M., Bureš, F. et al. 3,4-Dinitrothiophene as a central unit of quadrupolar push-pull-push systems. Chem Heterocycl Comp 53, 46–53 (2017). https://doi.org/10.1007/s10593-017-2020-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2020-1

Keywords

Search

Navigation