Dergiler / Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi / 2025 / Cilt: 29 Sayı: 3

Polar Uç Gruplara Sahip Yeni Üç-Halkalı Kalkon-İmin Türevlerinin Sentezi, Yapısal ve Mesomorfik Karakterizasyonu

Synthesis, Structural and Mesomorphic Characterization of New Three-Ring Chalcone-Imine Derivatives with Polar End Groups

Ceren Can Karanlık(YILDIZ TEKNİK ÜNİVERSİTESİ, FEN-EDEBİYAT FAKÜLTESİ)0000-0002-4821-5313
Sayfa
657–664
Yayın Tarihi
2025-12-25
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⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

Türevlerin mesomorfik davranışları diferansiyel taramalı kalorimetri (DSC) ve polarize optik mikroskop (POM) ile gözlemlenmiştir.

📌 3 Maddede Bu Makale

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Amaç & Hipotez:Bu çalışmada, uç pozisyonlardan birinde n-dodesiloksi grubu, diğerinde ise siyano veya brom grubu bulunan üç-benzen-halkalı merkezi üniteden oluşan yeni kalkon-imin türevleri sentezlenmiştir.
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Temel Bulgular & Veri:Elde edilen türevlerin kimyasal yapıları spektral analizlerle (1H-, 13C/APT-NMR ve FT-IR) aydınlatılmıştır.
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Sonuç & Katkı:Türevlerin mesomorfik davranışları diferansiyel taramalı kalorimetri (DSC) ve polarize optik mikroskop (POM) ile gözlemlenmiştir.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Sıvı kristaller · Kalkon-imin türevleri · Mesomorfik davranış

Özet

Bu çalışmada, uç pozisyonlardan birinde n-dodesiloksi grubu, diğerinde ise siyano veya brom grubu bulunan üç-benzen-halkalı merkezi üniteden oluşan yeni kalkon-imin türevleri sentezlenmiştir. Elde edilen türevlerin kimyasal yapıları spektral analizlerle (1H-, 13C/APT-NMR ve FT-IR) aydınlatılmıştır. Türevlerin mesomorfik davranışları diferansiyel taramalı kalorimetri (DSC) ve polarize optik mikroskop (POM) ile gözlemlenmiştir. Siyano-uçlu kalkon-imin türevinin (3a) 19 ˚C termal sıcaklık aralığı ile karakterize edilen enansiyotropik SmA mesofazını ve ayrıca M mesofazını sergilerken, brom-uçlu kalkon-imin türevinin (3b) ise herhangi bir mesomorfik davranış göstermediği belirlenmiştir. Bu sonuç, polar uç grubunun türü ve doğasının moleküllerin sıvı kristal özelliklerini büyük ölçüde etkilediğini vurgulamaktadır.

Abstract

In this study, new chalcone-imine derivatives composed of three-benzene-ring central unit containing n-dodecyloxy group at one end and cyano or bromo group at other end have been synthesized. Chemical structures of the obtained derivatives have been clarified by spectral analyses (1H-, 13C/APT-NMR and FT-IR). The mesomorphic behaviour and optical textures of the derivatives have been observed by differential scanning calorimetry (DSC) and polarized optical microscopy (POM). It was determined that cyano-terminated chalcone-imine derivative (3a) exhibits enantiotropic SmA mesophase, characterized by thermal range of 19 ˚C and also a M mesophase, while bromo-terminated chalcone-imine derivative (3b) does not show any mesomorphic behaviour. This result emphasizes that the type and the nature of the polar end group has a huge impact on the liquid crystalline properties of the molecules.

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Bu Makaleye Atıf Yap

Karanlık, C. C. (2025). Polar Uç Gruplara Sahip Yeni Üç-Halkalı Kalkon-İmin Türevlerinin Sentezi, Yapısal ve Mesomorfik Karakterizasyonu. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, Cilt: 29 Sayı: 3, 657–664. https://doi.org/10.19113/sdufenbed.1797499

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Kaynakça (43)

  1. Andrienko, D. 2018. Introduction to liquid crystals. Journal of Molecular Liquids, 267, 520–541.
  2. Kato, T., Mizoshita, N., Kishimoto, K. 2006. Functional Liquid‐Crystalline Assemblies: Self‐Organized Soft Materials. Angewandte Chemie International Edition, 45(1), 38–68.
  3. Kato, T. 2002. Self-Assembly of Phase-Segregated Liquid Crystal Structures. Science, 295, 2414–2418.
  4. Gurboga, B., Tuncgovde, E.B., Kemiklioglu, E. 2022. Liquid crystal‐based elastomers in tissue engineering. Biotechnology and Bioengineering, 119(4), 1047–1052.
  5. Leu, J.S.L., Teoh, J.J.X., Ling, A.L.Q., Chong, J., Loo, Y.S., Mat Azmi, I.D., Zahid, N.I., Bose, R.J.C., Madheswaran, T. 2023. Recent Advances in the Development of Liquid Crystalline Nanoparticles as Drug Delivery Systems. Pharmaceutics, 15(5), 1421.
  6. Wang, Z., Xu, T. Noel, A., Chen, Y.-C., Liu, T. 2021. Applications of liquid crystals in biosensing. Soft Matter, 17(18), 4675–4702.
  7. Fu, C., Li, D., Liu, C., Zhang, Y., Zhang, J., Cheng, Y. 2025. Chiral Co‐Assembled Liquid Crystal Polymer Network Enabled by In‐Situ Photopolymerization for High‐Performance CP‐OLEDs. Angewandte Chemie, 137(36).
  8. Denisov, I.G., Grinkova, Y. V., Lazarides, A.A., Sligar, S.G. 2004. Directed Self-Assembly of Monodisperse Phospholipid Bilayer Nanodiscs with Controlled Size. Journal of the American Chemical Society, 126(11), 3477–3487.
  9. Matharu, A.S., Jeeva, S., Ramanujam, P.S. 2007. Liquid crystals for holographic optical data storage. Chemical Society Reviews, 36(12), 1868.
  10. Ahmed, H.A., Mansour, E., Hagar, M. 2020. Mesomorphic study and DFT simulation of calamitic Schiff base liquid crystals with electronically different terminal groups and their binary mixtures. Liquid Crystals, 47(14-15), 2292–2304.
  11. Veerabhadraswamy, B.N., Rao, D.S.S., Prasad, S.K., Yelamaggad, C. V. 2015. Optically active, three-ring calamitic liquid crystals: the occurrence of frustrated, helical and polar fluid mesophases. New Journal of Chemistry, 39(3), 2011–2027.
  12. Zaki, A.A., Hagar, M., Alnoman, R.B., Jaremko, M., Emwas, A.-H., Ahmed, H.A. 2020. Mesomorphic, Optical and DFT Aspects of Near to Room-Temperature Calamitic Liquid Crystal. Crystals, 10(11), 1044.
  13. Foo, K.-L., Ha, S.-T., Yeap, G.-Y. 2022. Synthesis and phase transition behavior of calamitic liquid crystals containing heterocyclic core and lateral ethoxy substituent. Phase Transitions, 95(2), 178–192.
  14. Trân, H.Q., Kawano, S., Thielemann, R.E., Tanaka, K., Ravoo, B.J. 2024. Calamitic Liquid Crystals for Reversible Light‐Modulated Phase Regulation Based on Arylazopyrazole Photoswitches. Chemistry – A European Journal, 30(2).
  15. Rothera, J.G., Yu, J., AlNajm, K., Butrus, R., Ahangari‐Bashash, E., Watanabe, L.K., Rawson, J.M., Dmitrienko, A., Vukotic, V.N., Eichhorn, S.H. 2025. Core‐Only Calamitic Liquid Crystals: Molecular Design and Optoelectronic Properties. Chemistry – An Asian Journal, 20(8).
  16. Al-Zahrani, S.A., Khan, M.T., Jevtovic’, V., Masood, N., Jeilani, Y.A., Ahmed, H.A. 2023. Design of Liquid Crystal Materials Based on Palmitate, Oleate, and Linoleate Derivatives for Optoelectronic Applications. Molecules, 28(4) 1744.
  17. Bisoyi, H.K., Li, Q. 2022. Liquid Crystals: Versatile Self-Organized Smart Soft Materials. Chemical Reviews, 122(5), 4887–4926.
  18. Bubnov, A., Cigl, M., Mironov, S., Otruba, M., Penkov, D., Pacherová, O., Bohmová, Z., Hamplová, V. 2023. The correlations between the molecular core structure and mesomorphic behaviour for chiral liquid crystals with several (S)-lactate groups. Journal of Molecular Liquids, 387, 122590.
  19. Al-Mutabagani, L.A., Alshabanah, L.A., Gomha, S.M., Abolibda, T.Z., Shaban, M., Ahmed, H.A. 2021. Synthesis and Mesomorphic and Electrical Investigations of New Furan Liquid Crystal Derivatives. Frontiers in Chemistry, 9.
  20. Han, Z.-Y., Kun, S.-Q., Kang, J.-T., Jia, Y.-G. 2022. New (-)-menthol-based blue phase liquid crystals with different polar substituents in the terminal group: Synthesis, mesophase behaviors, and DFT calculations. Journal of Molecular Structure, 1263, 133147.
  21. Ali, M.H., Saad, G.R., Ahmed, N.H.S., Fahmi, A.A. 2023. Synthesis and physico-chemical properties of dilateral flouro azo/ester four aromatic ring mesogens and their mixtures of liquid crystals. Liquid crystals, 50(5), 737–753.
  22. Srinivasa, H.T. 2022. Polar cyano/nitrile group-derived rod-shaped nematic liquid crystals: synthesis and characterizations†. Molecular Crystals and Liquid Crystals, 737(1), 11–22.
  23. Wu, R., Xiong, G., Chen, Y., Wang, S. 2024. Control Patterning of Cyanobiphenyl Liquid Crystals for Electricity Applications. Langmuir, 40(41), 21693–21700.
  24. Kress, K.C., Kaller, M., Axenov, K. V., Tussetschläger, S., Laschat, S. 2012. Synthesis and mesomorphic properties of calamitic malonates and cyanoacetates tethered to 4-cyanobiphenyls. Beilstein Journal of Organic Chemistry, 8, 371–378.
  25. Paterson, D.A., Abberley, J.P., Harrison, W.T., Storey, J.M., Imrie, C.T. 2017. Cyanobiphenyl-based liquid crystal dimers and the twist-bend nematic phase. Liquid Crystals, 1–20.
  26. Pathak, G., Phettong, B., Chattham, N. 2025. Optimization of 4-Cyano-4’-pentylbiphenyl Liquid Crystal Dispersed with Photopolymer: Application Towards Smart Windows and Aerospace Technology. Polymers, 17(16), 2232.
  27. Alaasar, M., Tschierske, C. 2019. Nematic phases driven by hydrogen-bonding in liquid crystalline nonsymmetric dimers. Liquid crystals, 46(1), 124–130.
  28. Hagar, M., Ahmed, H.A., Alnoman, R.B., Jaremko, M., Emwas, A.-H., Sioud, S., Abu Al-Ola, K.A. 2021. New Liquid Crystal Assemblies Based on Cyano-Hydrogen Bonding Interactions. Frontiers in Chemistry, 9.
  29. Sezgin, B., Can Karanlık, C., Karanlık, G. 2025. Exploring the mesophase and optical behavior of novel furan-based chalcone liquid crystals with ester/azo linkages. New Journal of Chemistry, 49(29), 12676–12687.
  30. Wan, D., Liang, L., Mo, L., Che, Z., Hu, M., Li, J., Li, J. 2025. Synthesis and properties of high birefringence vinylene-bridged fluorinated terphenyl liquid crystals. Journal of Molecular Structure, 1345, 141668.
  31. Pytlarczyk, M., Kula, P. 2019. Synthesis and mesomorphic properties of 4,4”-dialkynyl-2’,3’-difluoro-p-terphenyls – the influence of C≡C acetylene linking bridge. Liquid Crystals, 46(4), 618–628.
  32. Habeeb, H.Q.A., Tomi, I.H.R. 2025. A new series of asymmetric calamitic esters based on 1,3,4-thiadiazole: synthesis, characterisation, and study of their thermo-optic properties. Liquid Crystals, 1–12.
  33. Patil N, V., Sahoo, R., Veerabhadraswamy, B.N., Chakraborty, S., Dhar, R., Mathad, R.D., Yelamaggad, C. V. 2021. Polarization of three- ring Schiff base ferroelectric liquid crystals. Liquid Crystals, 48(8), 1194–1205.
  34. Shirodkar, M.J., Bhat, K.S., Bhattacharjee, D., Sonali, M.K., Mahesha, M.G., Bhagavath, P. 2025. Mesomorphic and DFT study of new difluoro substituted Schiff base liquid crystals. Scientific Reports, 15(1), (2025) 15540.
  35. Panchal, J.C., Chaudhary, M.Y., Patel, H.N., Patel, T.M., Thakur, S., Mittal, S., Vyas, K.M., Sangani, C.B., Ahmed, S. 2025. Synthesis of new liquid crystal Schiff’s bases bearing ester moiety, DFT calculation and mesomorphic studies. Journal of Molecular Structure, 1321, 140078.
  36. Fadhil, M.Z.A.M., Mustamin, M.A., Jamain, Z. 2024. Liquid crystalline behaviour of symmetrical thermotropic Schiff base compounds. Journal of Molecular Structure, 1315, 138929.
  37. Ahmed, H.A., Aboelnaga, A. 2022. Synthesis and mesomorphic study of new phenylthiophene liquid crystals. Liquid Crystals, 49(6), 804–811.
  38. Zhu, X., Yin, F., Zhao, H., Chen, S., Bian, Z. 2017. Some new azobenzene liquid crystals involving chalcone and ester linkages. RSC Adv., 7(73), 46344–46353.
  39. Palahally Thimmappa, S. Sangarashettihalli Krishnegowda, G., Sudhir, A., Hemavathi Nagaraju, D. 2025. Chalcone based liquid crystalline compounds beyond biological applications: a review. Liquid Crystals, 52(5-6), 453–477.
  40. Katariya, K.D., Nakum, K.J., Hagar, M. 2022. New thiophene chalcones with ester and Schiff base mesogenic Cores: Synthesis, mesomorphic behaviour and DFT investigation. Journal of Molecular Liquids, 359, 119296.
  41. Katariya, K.D., Nakum, K.J., Soni, H., Nada, S., Hagar, M. 2023. Imine based Four-Ring Chalcone-Ester liquid Crystals: Synthesis, Characterization, mesomorphic behaviour and DFT approach. Journal of Molecular Liquids, 380, 121719.
  42. Bashir, N., Hameed, S., Muhammad, K., Vieira, A.A., Bechtold, I.H., Hameed, S. 2023. 4-(Aroyloxybenzoyloxy)benzonitriles with pronounced homeotropic SmA alignment. Liquid Crystals, 50(11-12), 1806–1813.
  43. Tanaka, S., Takezawa, Y., Kanie, K., Muramatsu, A. 2023. Forming a Homeotropic SmA Structure of Liquid Crystalline Epoxy Resin on an Amine-Modified Surface. ACS Omega, 8(36), 32365–32371.