Synthesis and self-assembly properties of thiacrown-cyclized tetrathiafulvalene organogelators

References

• Wang HH, Xue L, Jiang H. Ratiometric fluorescent sensor for silver ion and its resultant complex for iodide anion in aqueous solution. Org Lett. 2011;13(15):3844–3847.
   PubMed Web of Science ®Google Scholar
• Bader K, Neidhardt MM, Wohrle T, et al. Amino acid/crown ether hybrid materials: how charge affects liquid crystalline self-assembly. Soft Matter. 2017;13(45):8379–8391.
   PubMed Web of Science ®Google Scholar
• Lee S, Lee JS, Lee CH, et al. Nonpolymeric thermosensitive benzenetricarboxamides. Langmuir. 2011;27(5):1560–1564.
   PubMed Web of Science ®Google Scholar
• Yan XZ, Xu DH, Chi XD, et al. A multiresponsive, shape-persistent, and elastic supramolecular polymer network gel constructed by orthogonal self-assembly. Adv Mater. 2012;24(3):362–369.
   PubMed Web of Science ®Google Scholar
• Dong SY, Luo Y, Yan XZ, et al. A dual-responsive supramolecular polymer Gel formed by crown ether based molecular recognition. Angew Chem Int Edit. 2011;50(8):1905–1909.
   PubMed Web of Science ®Google Scholar
• Zhang MM, Xu DH, Yan XZ, et al. Self-Healing supramolecular gels formed by crown ether based host-guest interactions. Angew Chem Int Edit. 2012;51(28):7011–7015.
   PubMed Web of Science ®Google Scholar
• Ji XF, Yao Y, Li JY, et al. A supramolecular cross-linked conjugated polymer network for multiple fluorescent sensing. J Am Chem Soc. 2013;135(1):74–77.
   PubMed Web of Science ®Google Scholar
• Yan XZ, Xu DH, Chen JZ, et al. A self-healing supramolecular polymer gel with stimuli-responsiveness constructed by crown ether based molecular recognition. Polym Chem. 2013;4(11):3312–3322.
   Web of Science ®Google Scholar
• Cazacu A, Legrand YM, Pasc A, et al. Dynamic hybrid materials for constitutional self-instructed membranes. P Natl Acad Sci USA. 2009;106(20):8117–8122.
   PubMed Web of Science ®Google Scholar
• Sobczuk AA, Tamaru S, Shinkai S. New strategy for controlling the oligothiophene aggregation mode utilizing the gel-to-sol phase transition induced by crown-alkali metal interactions. Chem Comm. 2011;47(11):3093–3095.
   PubMed Web of Science ®Google Scholar
• Akutagawa T, Ohta T, Hasegawa T, et al. Formation of oriented molecular nanowires on mica surface. P Natl Acad Sci USA. 2002;99(8):5028–5033.
   PubMed Web of Science ®Google Scholar
• Akutagawa T, Kakiuchi K, Hasegawa T, et al. Molecularly assembled nanostructures of a redox-active organogelator. Angew Chem Int Edit. 2005;44(44):7283–7287.
   PubMed Web of Science ®Google Scholar
• Yang XY, Zhang GX, Li LQ, et al. Self-Assembly of a dendron-attached tetrathiafulvalene: gel formation and modulation in the presence of chloranil and metal ions. Small. 2012;8(4):578–584.
   PubMed Web of Science ®Google Scholar
• Liu YC, Liu ZX, Wang Y, et al. A tetrathiafulvalene-L-glutamine conjugated derivative as a supramolecular gelator for embedded C60 and absorbed rhodamine B. New J Chem. 2020;44(33):14151–14160.
   Web of Science ®Google Scholar
• Canevet D, del Pino AP, Amabilino DB, et al. Boosting electrical conductivity in a gel-derived material by nanostructuring with trace carbon nanotubes. Nanoscale. 2011;3(7):2898–2902.
   PubMed Web of Science ®Google Scholar
• Otsubo T, Ogura F. Crowned tetrathiafulvalene derivatives. Bull Chem Soc Jpn. 1985;58(4):1343–1344.
   Web of Science ®Google Scholar
• Nakamura T, Akutagawa T, Honda K, et al. A molecular metal with ion-conducting channels. Nature. 1998;394(6689):159–162.
   Web of Science ®Google Scholar
• Jeppesen JO, Nielsen MB, Becher J. Tetrathiafulvalene cyclophanes and cage molecules. Chem Rev. 2004;104(11):5115–5131.
   PubMed Web of Science ®Google Scholar
• Jorgensen T, Hansen TK, Becher J. Tetrathiafulvalenes as building-blocks in supramolecular chemistry. Chem Soc Rev. 1994;23(1):41–51.
   Web of Science ®Google Scholar
• Bryce MR, Batsanov AS, Finn T, et al. Crown-annelated 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene derivatives as cation sensors: synthesis, X-ray crystal structures, voltammetric and spectroscopic monitoring of metal complexation. Eur J Org Chem. 2001;2001(5):933–940.
   Web of Science ®Google Scholar
• Liu YC, Yin ZR, Jin LY, et al. Monopyrrolotetrathiafulvalene-based supramolecular organogels: multi-stimuli responsiveness and formation of charge-transfer salt gels. Dyes Pigments. 2017;140:500–511.
   Web of Science ®Google Scholar
• Kong DY, Xia Y, Li DF, et al. Super organogelator based on tetrathiafulvalene with four amide derivatives and its F4TCNQ charge-transfer complex. Supramol Chem. 2017;29(2):102–110.
   Web of Science ®Google Scholar
• Wei FZ, Wang L, Xia Y, et al. Synthesis and mesocrystalline properties of liquid crystal compounds with tetrathiafulvalene and two cyanobiphenyl units. J Sulfur Chem. 2020;41(1):19–28.
   Web of Science ®Google Scholar
• Hansen TK, Jorgensen T, Stein PC, et al. Crown ether derivatives of tetrathiafulvalene. 1. J Org Chem. 1992;57(24):6403–6409.
   Web of Science ®Google Scholar
• Liu YC, Liu LH, Zhu EW, et al. Gel formed by self-assembly of a urea-modified monopyrrolotetrathiafulvalene derivative displays multi-stimuli responsiveness and absorption of rhodamine B. ChemPlusChem. 2018;83(12):1109–1118.
   PubMed Web of Science ®Google Scholar
• Liu YC, Zheng NJ, Li HD, et al. Supramolecular gels based on monopyrrolotetrathiafulvalene and its TCNQ charge-transfer complex. Soft Matter. 2013;9(21):5261–5269.
   Web of Science ®Google Scholar
• Liu YC, Zheng NJ, Chen T, et al. Monopyrrolotetrathiafulvalene-succinamide conjugates and their TCNQ charge transfer complex based supramolecular gels with multiple stimulus responsiveness. Org Biomol Chem. 2014;12(35):6927–6936.
   PubMed Web of Science ®Google Scholar
• Liu YC, Lei WW, Chen T, et al. Poly(aryl ether) dendrons with monopyrrolotetrathiafulvalene unit-based organogels exhibiting gel-induced enhanced emission (GIEE). Chem Eur J. 2015;21(43):15235–15245.
   PubMed Web of Science ®Google Scholar
• Wang C, Zhang DQ, Zhu DB. A low-molecular-mass gelator with an electroactive tetrathiafulvalene group: tuning the gel formation by charge-transfer interaction and oxidation. J Am Chem Soc. 2005;127(47):16372–16373.
   PubMed Web of Science ®Google Scholar
• Puigmarti-Luis J, del Pino AP, Laukhin V, et al. Solvent effect on the morphology and function of novel gel-derived molecular materials. J Mater Chem. 2010;20:466–474.
   Web of Science ®Google Scholar