Skip to main content
SpringerLink
Log in

Dye spectra of benzene derivatives in the liquid-crystalline phase of 4-n-pentyl-4΄-cyanobiphenyl

  • Regular Article - Soft Matter
  • Published:
The European Physical Journal E Aims and scope Submit manuscript

Abstract

In the present paper, we study the interaction of associates (dimers and trimers) of 4-n-pentyl-4΄-cyanobiphenyl (5CB) with 1, 2-Diamino-4-nitrobenzene and N, N-Dimethyl-4-nitrosoaniline dye molecules. The structures of the intermolecular complexes were studied using hybrid functionals of the DFT method M06 and B3LYP with the 6–31 + G (d) basis set. The intermolecular binding energy of dyes with associates depends on the structure of the complexes and is about 5 kcal/mol. Vibrational spectra were calculated for all intermolecular systems. The electronic absorption spectra of dyes are sensitive to the structure of the mesophase. The pattern of the spectrum changes depending on the structure of the complex of the dimer or trimer with the dye molecule. The long-wavelength transition bands are characterized by shifts that are bathochromic for 1, 2-Diamino-4-nitrobenzene and hypsochromic for N, N-Dimethyl-4-nitrosoaniline.

Graphical Abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

Data availability

The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

References

  1. M. Morsy, G. Oweimreen, J. Hwang, Nonmesomorphic solute−mesomorphic solvent interactions studies. 2. ESR studies on the different phases of 5CB, 6CB, 7CB, and 8CB liquid crystals using PD−tempone and tempo−palmitate as probes. Structural and conformational effects. J. Phys. Chem. 100(20), 8331–8337 (1996)

    Article  Google Scholar 

  2. M. Kwak, Y. Kim, S. Han et al., Past, present, and future of WCG technologyin display. J. Soc. Inf. Displ. 27, 1–9 (2019)

    Article  Google Scholar 

  3. N. Hanemann, W. Haase, I. Svoboda, H. Fuess, Crystal structure of 4-pentyl-4’-cyanobiphenyl (5CB). Liq. Cryst. 19(5), 699–702 (1995)

    Article  Google Scholar 

  4. K. Inglot, T. Martyński, D. Bauman, Molecular aggregation in langmuir-blodgett films of azo dye/liquid crystal mixtures. Dyes Pigment. 17(2), 120–128 (2009)

    Google Scholar 

  5. P. Upadhyay, M. Rastogi, D. Kumar, Polarizability study of nematic liquid crystal 4-cyano-4′-pentylbiphenyl (5CB) and its nitrogen derivatives. Chem. Phys. 456, 41–46 (2015)

    Article  Google Scholar 

  6. O. Oltulu, F. Cakirtas, N. Yorulmaz, S. Yilmaz, Visible spectroscopy of 5CB/8CB liquid crystals. Phase Transit. 89(3), 242–248 (2016)

    Article  Google Scholar 

  7. D. Ojha, The interesting property of strong polar group nematogens in organic solvents–a computational study. Mol. Cryst. Liq. Cryst. 591(1), 1–9 (2014)

    Article  Google Scholar 

  8. P. Praveen, D. Ojha, Role of molecular interactions and end chain length on the photosensitivity of liquid crystalline alkyl cyanobiphenyl dimers–UV absorption-based approach through DFT calculations. Phase Transit. 87(7), 641–655 (2014)

    Article  Google Scholar 

  9. M.A. Kamarudin, A.A. Khan, S.M. Said, M.M. Qasim, T.D. Wilkinson, Composite liquid crystal-polymer electrolytes in dyesensitised solar cells: effects of mesophase alkyl chain length. Liq. Cryst. 45(1), 112–121 (2018)

    Article  Google Scholar 

  10. A. Adamow, L. Sznitko, E. Chrzumnicka et al., The ultra-photostable and electrically modulated stimulated emission in perylene-based dye doped liquid crystal. Sci. Rep. 9, 2143 (2019)

    Article  ADS  Google Scholar 

  11. E. Białecka-Florjańczyk, E. Wolarz, D. Bauman, Synthesis and thermal properties of twin compounds, alkanediacids 4-(4’-cyano)-biphenyl diesters. Z. Naturforsch. B 53(10), 1213–1215 (1998). https://doi.org/10.1515/znb-1998-1018

    Article  Google Scholar 

  12. T. Chandrakumar, L. Smith, E.E. Burnell, An orientational study of small solutes in zero electric field gradient nematic liquid-crystal mixtures. J. Phys. Chem. 99, 7054–7059 (1995). https://doi.org/10.1021/j100018a043

    Article  Google Scholar 

  13. R. Hertmanowski, E. Chrzumnicka, T. Martyński, D. Bauman, Self-aggregates formation of 3,4,9,10-tetra-(n-alkoxy-carbonyl)-perylenes in Langmuir-Blodgett films. J. Lumin. 126(2), 323–332 (2007)

    Article  Google Scholar 

  14. E.M. Averyanov, Orientational order and polarizability of molecules in a nematic liquid crystal. Phys. Solid State 56, 1058–1063 (2014). https://doi.org/10.1134/S1063783414050035

    Article  ADS  Google Scholar 

  15. D. Bauman, The study of the guest effect on the nematic phase stabilization. Mol. Cryst. Liq. Cryst. Incorp. Nonlinear Opt. 159, 197–217 (1988)

    Article  Google Scholar 

  16. S. Sousa, P. Fernandes, M. Ramos, General performance of density functional. J. Phys. Chem. A 111(42), 10439–10452 (2007)

    Article  Google Scholar 

  17. A.D. Becke, Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A 38, 3098–3100 (1988)

    Article  ADS  Google Scholar 

  18. S. Grimme, Density functional theory with London dispersion corrections. Wiley Interdiscip. Rev. Comput. Mol. Sci. 1(2), 211–228 (2011)

    Article  Google Scholar 

  19. S. Prasad, D. Ojha, Geometric structures, vibrational spectroscopic and global reactivity descriptors of nematogens containing strong polar group–a comparative analysis using DFT, HF and MP2 methods. Mol. Cryst. Liq. Cryst. 666(1), 12–28 (2018)

    Article  Google Scholar 

  20. M.T. Sims, L.C. Abbott, S.J. Cowling, J.W. Goodby, J.N. Moore, Dyes in liquid crystals: experimental and computational studies of a guest-host system based on a combined DFT and MD approach. Chem. Eur. J. 21(28), 10123–10130 (2015). https://doi.org/10.1002/chem.201406372

    Article  Google Scholar 

  21. A. Bendi, S. Atri, G.B.D. Rao, M.J. Raza, N. Sharma, Ultrasound-accelerated, concise, and highly efficient synthesis of 2-oxazoline derivatives using heterogenous calcium ferrite nanoparticles and their DFT studies. J. Chem. (2021). https://doi.org/10.1155/2021/7375058

    Article  Google Scholar 

  22. R. Veligeti, J.S. Anireddy, R.B. Madhu, D.S. Ramakrishna, One pot, three component synthesis of fluoro and trifluoromethyl substituted unsymmetrical dihydropyrazine fused acridine-3-carboxamide using renewable 2-MeTHF solvent and their DFT studies. J. Fluor. Chem. 261, 110019 (2022). https://doi.org/10.1016/j.jfluchem.2022.110019

    Article  Google Scholar 

  23. A. Bendi, G.B.D. Rao, N. Sharma, R. Tomar, L. Singh, Solvent-free synthesis of glycoside annulated 1,2,3-triazole based dihydropyrimidinones using copper ferrite nanomaterials as heterogeneous catalyst and dft studies. Chem. Eur. 7(7), e202103910 (2022)

    Google Scholar 

  24. P. Praveen, D. Ramakrishna, D. Ojha, UV spectral characterization of a smectic-C liquid crystal: theoretical support to the experiment. Mol. Cryst. Liq. Cryst. 643(1), 76–82 (2017)

    Article  Google Scholar 

  25. P. Praveen, D. Ojha, Photosensitivity, substituent and solvent-induced shifts in UV-visible absorption bands of naphthyl-ester liquid crystals: a comparative theoretical approach. Liq. Cryst. 41(6), 872–882 (2014)

    Article  Google Scholar 

  26. R. Chen, Z. An, W. Wang, X. Chen, P. Chen, Improving UV stability of tolane-liquid crystals in photonic applications by the ortho fluorinesubstitution. Opt. Mater. Express 6(1), 97–105 (2016)

    Article  ADS  Google Scholar 

  27. T. Shabatina, E. Vovk, N. Kovalevskaya, G. Sergeev, The electronic absorption spectra and molecular aggregate formation in vacuum deposited films of mesogenic cyanobiphenyls and their solutions. Mol. Cryst. Liq. Cryst. 366, 255–262 (2001)

    Article  Google Scholar 

  28. T. Andreeva, M. Bedrina, Change of structural and spectral characteristics in the liquid crystal phase under the influence of an electric field. Stability and Control Processes in Memory of V.I. Zubov (SCP), (IEEE, St-Petersburg, 2015), p. 506–507

  29. T.I. Shabatina, E.V. Vovk, G.N. Andreev et al., IR spectroscopic study of molecular associates of mesogenic cyanophenyls. J. Struct. Chem. 39, 318–322 (1998). https://doi.org/10.1007/BF02873637

    Article  Google Scholar 

  30. C. Zezhang, J. Yurong, L. Meng, J. Lulu, M. Heng, Molecular vibration mode assignment of nematic liquid crystal 5CB on terahertz spectra. Liq. Cryst. 42(7), 947–953 (2015)

    Article  Google Scholar 

  31. L. Babkova, I. Gnatyuk, S. Trukhacheva, Investigation of 4′-n-alkyl-4-cyanobiphenyls structure features by IR spectroscopy methods. J. Mol. Struct. 744(747), 425–432 (2005)

    Article  ADS  Google Scholar 

  32. L. Babkov, I. Gnatyuk, G. Puchkovska, S. Truckhachev, The investigation of the 4-butil-4’-cyanobiphenyl IR spectra transformations at the temperature changes. Izv. Sarat. Univ. New Ser. Phys. 8, 42–47 (2008). https://doi.org/10.18500/1817-3020-2008-8-1-42-47

    Article  Google Scholar 

  33. T. Andreeva, M. Bedrina, Structure and optical properties of the 4-cyano-4′-n-pentylbiphenyl dimers and trimers. Liq. Cryst. 47(1), 125–135 (2020). https://doi.org/10.1080/02678292.2019.1631966

    Article  Google Scholar 

  34. Y. Zhao, D.G. Truhlar, The M06 suite of density functional for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functional and systematic testing of four M06-class functional and 12 other functional. Theor. Chem. Acc. 120, 215–241 (2008)

    Article  Google Scholar 

  35. T. Andreeva, M. Bedrina, The influence of hybrid potentials of the DFT method on the results of study of liquid crystal phase of a substance. Vestn. SPbSU 10(16), 16–24 (2015)

    Google Scholar 

  36. V. Maslov, Interpretation of the electronic spectra of Fe and Co porphyrins based on quantum-chemical calculations by the density functional method. Opt. Spektrosk. 105(2), 163–170 (2008)

    Article  ADS  Google Scholar 

  37. T. Andreeva, M.E. Bedrina, D.A. Ovsyannikov, Comparative analysis of calculation methods in electron spectroscopy. Vestn. St. Petersbg. Univ. Appl. Math. Comput. Sci. Control Process. 15(4), 518–528 (2019). https://doi.org/10.21638/11702/spbu10.2019.408

    Article  Google Scholar 

  38. M.J. Frisch et al., Gaussian 09, Rev D.01 Gaussian (Inc, Wallingford, CT, 2013)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Saint Petersburg State University, Saint Petersburg, Russia

    Tatiana A. Andreeva, Marina E. Bedrina & Nikolay V. Egorov

Authors
  1. Tatiana A. Andreeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marina E. Bedrina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nikolay V. Egorov
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

All the authors were involved in the preparation of the manuscript.

Corresponding author

Correspondence to Tatiana A. Andreeva.

Ethics declarations

Conflict of interest

No potential conflict of interest was reported by the authors.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Andreeva, T.A., Bedrina, M.E. & Egorov, N.V. Dye spectra of benzene derivatives in the liquid-crystalline phase of 4-n-pentyl-4΄-cyanobiphenyl. Eur. Phys. J. E 46, 45 (2023). https://doi.org/10.1140/epje/s10189-023-00305-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1140/epje/s10189-023-00305-7

Search

Navigation