Structure variation on self-assembly and optical properties of bent hexacatenars with dicyanothiophene bent core and amide links

References

• a) Goodby, J. W.; Tschierske, C.; Raynes.; Gleeson, H.; Kato, T.; Collings, P. J. Laterally Alkyl- and Aryl-Substituted, Swallow-Tailed, and Polycatenar Mesogens: Structural Features and Functionalities. In Handbook of Liquid Crystals; Demus, D., Goodby, J., Gray, G. W., Spiess, H. W., Vill, V., Eds.; 2014; pp. 1-86; b) Nguyen, H. T.; Destrade, C.; Malthete, J. Phasmids and Polycatenar Mesogens. Adv. Mater. 1997, 9, 375–388. DOI: 10.1002/adma.19970090503; c) Zhang, D.; Liu, J.; Gao, S. Y.; Bermeshev, M. V.; Chen, Z. J.; Ren, X. K. Siloxane Tethered Perylene Diimide: From Monotropic Phase Structures to Tunable Photoconductivity. J. Mater. Chem. C 2021, 9, 9236–9241. DOI: 10.1039/D1TC00822F; d) Eccher, J.; Zajaczkowski, W.; Faria, G. C.; Bock, H.; Seggern, H. V.; Pisula, W.; Bechtold, I. H. Thermal Evaporation Versus Spin-Coating: Electrical Performance in Columnar Liquid Crystal OLEDs. ACS Appl. Mater. Interfaces 2015, 7, 16374–16381. DOI: 10.1021/acsami.5b03496.
   Google Scholar
• a) Kotian, S. Y.; Mohan, C. D.; Merlo, A. A.; Rangappa, S.; Nayak, S. C.; Rai, K. M. L.; Rangappa, K. S. Small Molecule Based Five-Membered Heterocycles: A View of Liquid Crystalline Properties beyond the Biological Applications. J. Mol. Liq. 2020, 297, 111686. DOI: 10.1016/j.molliq.2019.111686; b) Gupta, R. K.; Sudhakar, A. A. Perylene-Based Liquid Crystals as Materials for Organic Electronics Applications. Langmuir 2019, 35, 2455–2479. DOI: 10.1021/acs.langmuir.8b01081; c) Xiao, Y.; Tan, X.; Xing, W.; Zhao, K.; Zhang, B.; Cheng, X. Coumarin-based Emissive Hexacatenars: Synthesis, 2D and 3D Self-Assembly and Photodimerization. J. Mater. Chem. C 2018, 6, 10782–10792. DOI: 10.1039/C8TC04040K; d) Zhang, B.; Xiao, Y.; Fang, H.; Gao, H.; Wang, F.; Cheng, X. Mesogenic D-A Fluorophores based on Cyanovinyl and Benzothiadiazole. New J. Chem. 2018, 42, 16709–16716. DOI: 10.1039/C8NJ02814A; e) Chen, H.; Zhang, R.; Gao, H.; Cheng, H.; Fang, H.; Cheng. X.; Synthesis, Self-Assembly, Metal Binding Properties of Triazole Azobenzene based Polycatenar Dyes through Click Chemistry. Dyes Pigm. 2018, 149, 512–520. DOI: 10.1016/j.dyepig.2017.10.025; f) Zhao, K.; Xiao, Y.; Guo, C.; Chang, Q.; Gao, H.; Cheng, X. Control the Self-Assembly of Fluorenone-Based Polycatenars by Tuning Chain Length. Tetrahedron 2019, 75, 409–415. DOI: 10.1016/j.tet.2018.12.009; g) Xing, W.; Xiao, Y.; Zhao, K.; Kong, T.; Cheng, X. Control of Supramolecular Nanoassemblies by Tuning the Polarities of Linkages and Solvents. J. Mol. Liq. 2018, 272, 1–7. DOI: 10.1016/j.molliq.2018.09.008; h) Cheng, H.; Li, Y. X.; Zeng, X. B.; Gao, H.; Cheng, X.; Ungar, G. Trigonal Columnar Self-Assembly of Bent Phasmid Mesogens. Chem. Commun. 2018, 54, 156–159. DOI: 10.1039/C7CC06714C.
   Google Scholar
• a) Gim, M. J.; Hur, S. T.; Park. K. W.; Lee, M.; Choi, S. W.; Takezoe, H. Photoisomerization-Induced Stable Liquid Crystalline Cubic Blue Phase. Chem. Commun. 2012, 48, 9968–9970. DOI: 10.1039/C2CC34114J; b) Begum, N.; Kaur, S.; Mohiuddin, G.; Nandi, R.; Gupta, S. P.; Rao, N. V. S.; Pal, S. K. Structural Understanding, Photoswitchability, and Supergelation of a New Class of Four Ring-Based Bent-Shaped Liquid Crystal. J. Phys. Chem. B 2019, 123, 4443−4451. DOI: 10.1021/acs.jpca.9b03121; c) Alaasar, M.; Prehm, M.; Poppe, S.; Tschierske, C. Development of Polar Order by Liquid-Crystal Self-Assembly of Weakly Bent Molecules. Chem. Eur. J. 2017, 23, 5541–5556. DOI: 10.1002/chem.201606035; d) Blanco, H.; Iguarbe, V.; Barberá, J.; Serrano, J. L.; Elduque, A.; Giménez, R. Supramolecular Columnar Liquid Crystals with Tapered-Shape Simple Pyrazoles Obtained by Efficient Henry/Michael Reactions. Chem. Eur. J. 2016, 22, 4924–4930. DOI: 10.1002/chem.201504779; e) Ahipa, T. N.; Adhikari, A. V. New Cyanopyridone based Luminescent Liquid Crystalline Materials: Synthesis and Characterization. Photochem. Photobiol. Sci. 2014, 13, 1496–1508. DOI: 10.1039/C4PP00031E; f) Alaasar, M.; Poppe, S.; Kerzig, C.; Klopp, C.; Eremin, A.; Tschierske, C. Cluster Phases of 4-Cyanoresorcinol Derived Hockey-Stick Liquid Crystals. J. Mater. Chem. C 2017, 5, 8454-8468. DOI: 10.1039/C7TC01816A.
   Google Scholar
• Levitsky, I. A.; Kishikawa, K.; Eichhorn, S. H.; Swager, T. M. Exciton Coupling and Dipolar Correlations in a Columnar Liquid Crystal: Photophysics of a Bent-Rod Hexacatenar Mesogen. J. Am. Chem. Soc. 2000, 122, 2474–2479. DOI: 10.1021/ja993947d.
   Web of Science ®Google Scholar
• a) Eremina, A.; Jákli, A. Polar Bent-Shape Liquid Crystals – from Molecular Bend to Layer Splay and Chirality. Soft Matter 2013, 9, 615–637. DOI: 10.1039/C2SM26780B; b) Ocak, H.; Eran, B. B.; Nuray, S.; Özkonstanyan, A.; Poppe, S.; Tschierske, C. Extraordinary Magnetic Field Effects on the LC Phases of Homochiral and Racemic 4-Cyanoresorcinol-Based Diamagnetic Bent-Core Mesogens. J. Mater. Chem. C 2021, 9, 1895–1910. DOI: 10.1039/D0TC05355D; c) Miyajima, D.; Araoka, F.; Takezoe, H.; Kim, J.; Kato, K.; Takata, M.; Aida, T. Columnar Liquid Crystal with a Spontaneous Polarization along the Columnar Axis. J. Am. Chem. Soc. 2010, 132, 8530–8531. DOI: 10.1021/ja101866e; d) Araoka, F.; Masuko, S.; Kogure, A.; Miyajima, D.; Aida, T., Takezoe, H. High-Optical-Quality Ferroelectric Film Wet-Processed from a Ferroelectric Columnar Liquid Crystal as Observed by Non-linear-Optical Microscopy. Adv. Mater. 2013, 25, 4014–4017. DOI: 10.1002/adma.201301380.
   Google Scholar
• a) Lehmann, M.; Kang, S. W.; Köhn, C.; Haseloh, S.; Kolb, U.; Schollmeyer, D.; Wang, Q. B.; Kumare, S. Shape-Persistent V-Shaped Mesogens—Formation of Nematic Phases with Biaxial Order. J. Mater. Chem. 2006, 16, 4326–4334. DOI: 10.1039/B605718G; b) Seltmann, J.; Müller, K.; Klein, S.; Lehmann, M. V-Shaped Nematogens with the “Magic Bent Angle”. Chem. Commun. 2011, 47, 6680–6682. DOI: 10.1039/C1CC10577A; c) Begum, N.; Kaur, S.; Mohiuddin, G.; Nandi, R.; Gupta, S. P.; Rao, N. V. S.; Pal, S. K. Structural Understanding, Photoswitchability, and Supergelation of a New Class of Four Ring-Based Bent-Shaped Liquid Crystal. J. Phys. Chem. B 2019, 123, 4443–4451. DOI: 10.1021/acs.jpca.9b03121; d) Knöller, J. A.; Forschner, R.; Frey, W.; Lang, J.; Baro, A.; Zens, A.; Molard, Y.; Giesselmann, F.; Claasen, B.; Laschat, S. Chasing Self-Assembly of Thioether-Substituted Flavylium Salts in Solution and Bulk State, ChenPhysChem. 2022, 23, e202200154. DOI: 10.1002/cphc.202200154.
   Google Scholar
• a) Westphal, E.; Prehm, M.; Bechtold, I. H.; Tschierske, C.; Gallardo, H. Room Temperature Columnar Liquid Crystalline Phases of Luminescent Non-Symmetric Star-Shaped Molecules Containing Two 1,3,4-Oxadiazole Units. J. Mater. Chem. C 2013, 1, 8011–8022. DOI: 10.1039/C3TC31704H; b) Pathak, S. K.; Pradhan, B.; Gupta, M.; Pal, S. K.; Sudhakar, A. A. Liquid-Crystalline Star-Shaped Supergelator Exhibiting Aggregation-Induced Blue Light Emission. Langmuir 2016, 32, 9301–9312. DOI: 10.1021/acs.langmuir.6b02509; c) Ruan, Y.; Li, Q. H.; Shu, L.; Wan, J. H. A Shape-Persistent Arylene Ethynylene Macrocycle with a Multiple Acetamide Modified Cavity: Synthesis and Gelation. Soft Matter 2021, 17, 3242–3249. DOI: 10.1039/D0SM02144J.
   Google Scholar
• a) Miyajima, D.; Araoka, F.; Takezoe, H.; Kim, J.; Kato, K.; Takata, M.; Aida, T. Columnar Liquid Crystal with a Spontaneous Polarization along the Columnar Axis. J. Am. Chem. Soc. 2010, 132, 8530–8531. DOI: 10.1021/ja101866e; b) Araoka, F.; Isoda, M.; Miyajima, D.; Seo, I.; Oh-e, M.; Aida, T.; Takezoe, H. Polar Dynamics at a Functional Group Level: Infrared- Visible Sum-Frequency Generation Study on Polar Columnar Liquid Crystals. Adv. Electron. Mater. 2017, 3, 1600503. DOI: 10.1002/aelm.201600503.
   Google Scholar
• Miyajima, D.; Araoka, F.; Takezoe, H.; Kim, J.; Kato, K.; Takata, M.; Aida, T. Ferroelectric Columnar Liquid Crystal Featuring Confined Polar Groups within Core-Shell Architecture. Science. 2012, 336, 209–213. DOI: 10.1126/science.1217954.
   PubMed Web of Science ®Google Scholar
• a) Gopal, A.; Varghese, R.; Ajayaghosh, A. Oligo(p-phenylene-ethynylene)-Derived Super-π-Gelators with Tunable Emission and Self-Assembled Polymorphic Structures. Chem. Asian J. 2012, 7, 2061–2067. DOI: 10.1002/asia.201200410; b) Ziessel, R.; Pickaert, G.; Camerel, F.; Donnio, B.; Guillon, D.; Cesario, M.; Prange, T. Tuning Organogels and Mesophases with Phenanthroline Ligands and Their Copper Complexes by Inter- to Intramolecular Hydrogen Bonds. J. Am. Chem. Soc. 2004, 126, 12403–12413. DOI: 10.1021/ja047091a.
   Google Scholar
• Tan, X. P.; Kong, L. Y.; Dai, H.; Cheng, X. H.; Liu, F.; Tschierske, C. Triblock Polyphiles Through Click Chemistry: Self-Assembled Thermotropic Cubic Phases Formed by Micellar and Monolayer Vesicular Aggregates. Chem. Eur. J. 2013, 19, 16303–16313. DOI: 10.1002/chem.201301538.
   PubMed Web of Science ®Google Scholar
• Tian, Y. J.; Meijer, E. W.; Wang, F. Cooperative Self-Assembly of Platinum(ii) Acetylide Complexes. Chem. Commun. 2013, 49, 9197–9199. DOI: 10.1039/C3CC44997A.
   PubMed Web of Science ®Google Scholar
• Balandier, J. Y.; Quist, F.; Amato, C.; Bouzakraoui, S.; Cornil, J.; Sergeyev, S.; Geerts, Y. Synthesis of Soluble Oligothiophenes Bearing Cyano Groups, Their Optical and Electrochemical Properties. Tetrahedron. 2010, 66, 9560–9572. DOI: 10.1016/j.tet.2010.09.086.
   Web of Science ®Google Scholar
• Peng, X.; Gao, H.; Xiao, Y.; Cheng, H.; Huang, F.; Cheng, X. Synthesis and Self-Assembly of Photoresponsive and Luminescent Polycatenar Liquid Crystals Incorporating an Azobenzene Unit Interconnecting Two 1,3,4-Thiadiazoles. New. J. Chem. 2017, 41(5), 2004–2012. DOI: 10.1039/C6NJ02604D.
   Web of Science ®Google Scholar
• a) Raeburn, J.; Cardoso, A. Z.; Adams, D. J. The Importance of the Self-Assembly Process to Control Mechanical Properties of Low Molecular Weight Hydrogels. Chem. Soc. Rev. 2013, 42, 5143–5156. DOI: 10.1039/C3CS60030K; b) Buerkle, L.E.; Rowan, S. J. Supramolecular Gels Formed from Multi-Component Low Molecular Weight Species. Chem. Soc. Rev. 2012, 41, 6089–6102. DOI: 10.1039/C2CS35106D; c) Yu, G.; Yan, X.; Han, C.; Huang, F. Characterization of Supramolecular Gels. Chem. Soc. Rev. 2013, 42, 6697–6722. DOI: 10.1039/C3CS60080G.
   Google Scholar
• a) Faggi, E.; Sebastián, R. M.; Vallribera, A. Fluorous Gallic Acid Derivatives as Versatile Gelators. Self-Assembly into Nanosized Fibers or Balls. Tetrahedron 2010, 66, 5190–5195. DOI: 10.1016/j.tet.2010.04.086; b) Cheng, H. F.; Xing, W.; Zhang, B.; Yu, J.; Cheng, X. H. Bisphenylsulfone-based Polycatenar Mesogens via CuAAC Click Reaction: Self-Assembly and their Applications in Water Purification. Tetrahedron 2018, 74, 2735–2742. DOI: 10.1016/j.tet.2018.04.038.
   Google Scholar
• Marrocchi, A.; Seri, M.; Kim, C.; Facchetti, A.; Taticchi, A.; Marks, T. J. Low-Dimensional Arylacetylenes for Solution-Processable Organic Field-Effect Transistors. Chem. Mater. 2009, 21, 2592–2594. DOI: 10.1021/cm900734c.
   Web of Science ®Google Scholar