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Hydrogen-bonded ionic liquid crystals based on multi-armed structure: synthesis and characterization

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Abstract

A new type of six-armed π-conjugated structure was built up from benzene as the central core and electron-rich triazine rings as the peripheral group. The hexasubstituted product was liquid and did not exhibit any liquid crystal properties while the equimolar mixtures in 1:1 ratio of the hexasubstituted compound and 4-(dodecyloxy)benzoic acid resulted in an organic salt exhibiting a columnar mesophase characterized with a dendritic growing texture. Examination of the relationship between structure and properties and the presence of the number of carbon atoms in the alkyl chain suggested that, the higher increase led to the phase transition at low temperature to form a columnar mesophase as an ionic liquid crystal composed of cations and anions. These are often stabilized by resonance with strongly delocalized charges. The liquid crystalline properties of the organic salt were investigated by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM).

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References

  1. Giacomelli G, Porcheddu A, Luca LD (2004) Curr Org Chem 15:1497

    Article  Google Scholar 

  2. Shahbaz M, Urano S, LeBreton PR, Rossman MA, Hosmane RS, Leonard NJ (1984) J Am Chem Soc 106:2805

    Article  CAS  Google Scholar 

  3. Li J, Tao L, Wang Y, Yao Y, Guo Q (2021) Front Chem 18:482

    Google Scholar 

  4. Kroke E, Schwarz M, Horath-Bordon E, Kroll P, Noll B, Norman AD (2002) New J Chem 26:508

    Article  CAS  Google Scholar 

  5. Phillips RM (2016) Cancer Chemother Pharmacol 77:441

    Article  CAS  Google Scholar 

  6. Ide M, Kato T, Nakata M, Saito K, Yoshida T, Awaya T, Heike T (2015) Brain Dev 37:825

    Article  Google Scholar 

  7. Alazawi SK, Al-Jumaili MHA (2022) J Chem Res 7:1

    Google Scholar 

  8. Yan W, Zhao Y, He J (2018) Mol Med Rep 18:75

    Google Scholar 

  9. Abu-Aisheh NM, Mustafa SM, Mubarak SM, El-Abadelah MM, Voelter W (2012) Lett Org Chem 9:65

    Article  Google Scholar 

  10. Hynes J Jr, Dyckman AJ, Lin S, Wrobleski ST, Wu H, Gillooly KM, Kanner SB, Lonial H, Loo D, McIntyre KW, Pitt S (2008) J Med Chem 10:4

    Article  Google Scholar 

  11. Cascioferro S, Parrino B, Spanò V, Carbone A, Montalbano A, Barraja P, Diana P, Cirrincione G (2017) Eur J Med Chem 15:523

    Article  Google Scholar 

  12. Singla P, Luxami V, Paul K (2015) Eur J Med Chem 102:39

    Article  CAS  Google Scholar 

  13. Lim J, Kong SY, Yun YJ (2018) J Nanomater 25:2018

    Google Scholar 

  14. Wu C, Zhang H, Hu M, Shan G, Gao J, Liu J, Zhou X, Yang J (2020) Adv Electron Mater 6:2000253

    Article  CAS  Google Scholar 

  15. Zhang H, Zang XF, Hong YP, Chen ZE (2021) Synth Met 280:116882

    Article  CAS  Google Scholar 

  16. Li B, Lei Q, Qin T, Zhang X, Zhao D, Wang F, Li W, Zhang Z, Fan L (2021) CrystEngComm 23:8260

    Article  CAS  Google Scholar 

  17. Zhang M, Ren S, Guo Q, Shen B (2021) Microporous Mesoporous Mater 326:111395

    Article  CAS  Google Scholar 

  18. An ZF, Chen RF, Yin J, Xie GH, Shi HF, Tsuboi T, Huang W (2011) Chem Eur J 17:10871

    Article  CAS  Google Scholar 

  19. Akkurt N, Al-Jumaili MH, Eran BB, Ocak H, Torun L (2019) Turk J Chem 43:1436

    Article  CAS  Google Scholar 

  20. Akkurt N, Al-Jumaili MH, Ocak H, Cakar F, Torun L (2020) Turk J Chem 44:726

    Article  CAS  Google Scholar 

  21. Bakr EA, Al-Jumaili MH (2020) Mol Cryst Liq Cryst 710:40

    Article  CAS  Google Scholar 

  22. Sun C, Hudson ZM, Helander MG, Lu ZH, Wang S (2011) Organometallics 30:5552

    Article  CAS  Google Scholar 

  23. Banerjee R, Brown DR, Weerapana E (2013) Synlett 24:1599

    Article  CAS  Google Scholar 

  24. Steffensen MB, Hollink E, Kuschel F, Bauer M, Simanek EE (2006) Polym Chem 44:3411

    Article  CAS  Google Scholar 

  25. Janairo JI, Sakaguchi T, Mine K, Kamada R, Sakaguchi K (2018) Protein Pept Lett 25:4

    Article  CAS  Google Scholar 

  26. Al-Jumaili MH, Akkurt N, Torun L (2021) Monatsh Chem 152:551

    Article  CAS  Google Scholar 

  27. Kouvetakis J, Grotjahn D, Becker P, Moore S, Dupon R (1994) Chem Mater 6:636

    Article  CAS  Google Scholar 

  28. Couderc G, Hulliger J (2010) Chem Soc Rev 39:1545

    Article  CAS  Google Scholar 

  29. Whitesides GM, Simanek EE, Mathias JP, Seto CT, Chin D, Mammen M, Gordon DM (1995) Acc Chem Res 28:37

    Article  CAS  Google Scholar 

  30. Azhar U, Bashir MS, Babar M, Arif M, Hassan A, Riaz A, Mujahid R, Sagir M, Suri SU, Show PL, Chang JS (2022) Chemosphere 302:134792

    Article  CAS  Google Scholar 

  31. Al-Jumaili M, Hamed A, Akkurt N, Torun L (2020) Indones J Chem 20:705

    Article  CAS  Google Scholar 

  32. Sonoda M, Inaba A, Itahashi K, Tobe Y (2001) Org Lett 26:2419

    Article  Google Scholar 

Download references

Acknowledgements

Authors thank to Professor Belkis Bilgin Eran for valuable discussions on POM studies. The authors acknowledge the funding from the following agents. The Scientific and Technological research Council of Turkey (TUBITAK) with the project no. 114Z722 and The Office of Scientific Research of Yildiz Technical University, project no. FCD-2021-3892.

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Authors and Affiliations

  1. Department of Anesthesia Techniques, Dijlah University College, Baghdad, Iraq

    Mohammed Hadi Ali Al-Jumaili & Lokman Torun

  2. Chemistry Department, Yıldız Technical University, Faculty of Science and Art, 34220, Istanbul, Turkey

    Hale Ocak

  3. TORKİM ARGE Kimya Sanayi Tic. A. S. YTÜ Teknopark, Kuluçka Merkezi, Esenler, 34220, Istanbul, Turkey

    Lokman Torun

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  1. Mohammed Hadi Ali Al-Jumaili
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  2. Hale Ocak
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Correspondence to Lokman Torun.

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Al-Jumaili, M.H.A., Ocak, H. & Torun, L. Hydrogen-bonded ionic liquid crystals based on multi-armed structure: synthesis and characterization. Monatsh Chem 153, 939–947 (2022). https://doi.org/10.1007/s00706-022-02969-x

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  • DOI: https://doi.org/10.1007/s00706-022-02969-x

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