322
Views
5
CrossRef citations to date
0
Altmetric
Article

1,2,3-Triazole lamellar liquid crystal and its non-covalent palladium complex dimer: structure, mesomorphism and self-assembly properties

, , , ORCID Icon, , ORCID Icon, , , & show all
Pages 72-84 | Received 01 May 2021, Accepted 13 Jun 2021, Published online: 19 Jul 2021

References

  • Roy B, De N, Majumdar KC. Advances in metal-free heterocycle-based columnar liquid crystals. Chem Eur J. 2012;18(46):14560–14588.
  • Gallardo H, Westphal E. Importance of organic synthesis in the development of liquid crystals. Curr Org Synth. 2015;12(6):806–821.
  • Ghosh T, Lehmann M. Recent advances in heterocycle-based metal-free calamitics. J Mater Chem C. 2017;5(47):12308–12337.
  • Espinet P, Esteruelas MA, Oro LA, et al. Transition metal liquid crystals: advanced materials within the reach of the coordination chemist. Coordin Chem Rev. 1992;117:215–274.
  • Tritto E, Chico R, Sanz-Enguita G, et al. Alignment of palladium complexes into columnar liquid crystals driven by peripheral triphenylene substituents. Inorg Chem. 2014;53(7):3449–3455. .
  • Pucci D, Donnio B. Metal-containing liquid crystals, handbook of liquid crystals. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA; 2014. DOI:https://doi.org/10.1002/9783527671403.hlc077.
  • Gil MV, Arévalo MJ, López Ó. Click chemistry-what’s in a name? Triazole synthesis and beyond. Synthesis. 2007;11:1589–1620.
  • Cristiano R, de Oliveira Santos DMP, Conte G, et al. 1,4‐Diaryl and schiff’s base [1,2,3]-triazole derivative liquid crystalline compounds. Liq Cryst. 2006;33:997–1003.
  • Zhao KQ, Bai YF, Hu P, et al. Synthesis of triphenylene discotic liquid crystal dimers: click chemistry as an efficient tool. Mol Cryst Liq Cryst. 2009;509(1):77/[819]-888/[830]. .
  • Yu WH, Nie SC, Bai YF, et al. Synthesis of disk-rod-disk liquid crystal trimers by using click chemistry. Sci Chin Chem. 2010;53(5):1134–1141.
  • Yu WH, Chen C, Hu P, et al. Tetraphenylethene -triphenylene oligomers with an aggregation-induced emission effect and discotic columnar mesophase. RSC Adv. 2013;3:14099–14105.
  • Bai YF, Zhao KQ, Hu P, et al. Mono-disperse triphenylene discotic liquid crystal oligomers synthesized by click chemistry. Curr Org Chem. 2013;17(8):871–885.
  • Heng BT, Yeap GY, Mahmood WAK, et al. New heterocyclic metallomesogens: synthesis, mesomorphic and thermal behaviours of Cu(II) complexes with 1,2,3-triazole-based Schiff bases ligands. Liq Cryst. 2015;42(2):204–215. .
  • Alshargabi A, Yeap GY, Mahmood WAK, et al. Non-symmetrical liquid crystal dimers armed with azobenzene and 1,2,3-triazole-cholesterol. Liq Cryst. 2015;42(9):1337–1349. .
  • Rodrigues LD, Sunil D, Chaithra D, et al. 1,2,3/1,2,4-Triazole containing liquid crystalline materials: an up-to-date review of their synthetic design and mesomorphic behavior. J Mol Liq. 2020;297:111909.
  • Kotian SY, Mohan CD, Merlo AA, et al. Small molecule based five-membered heterocycles: a view of liquid crystalline properties beyond the biological applications. J Mol Liq. 2020;297:111686.
  • Gallardo H, Ely F, Bortoluzzi AJ, et al. Applying click chemistry to synthesis of chiral [1,2,3]‐triazole liquid crystals. Liq Cryst. 2005;32:667–671.
  • Majumdar KC, Mondal S, Sinha RK. Synthesis and characterization of novel cholesterol based mesogenic compounds using ‘click’ chemistry. New J Chem. 2010;34(7):1255–1260.
  • Yeap GY, Alshargabi A, Mahmood WAK, et al. Synthesis, characterization and molecular organization for induced smectic phase of triazole ring in non-symmetric liquid crystalline dimer. Tetrahedron. 2015;71(23):3939–3945. .
  • Cheng HM, Ma C, Chen Y, et al. Monosubstituted ferrocene liquid crystals containing click triazole with a wide nematic phase temperature range. Liq Cryst. 2017;44(9):1450–1461. .
  • Thevenet D, Neier R. Click chemistry applied in the synthesis of symmetrical triphenylene-based discotic liquid-crystalline dimers. Synthesis. 2011;23:3801–3806.
  • Umesh CP, Marcelis ATM, Zuilhof H. Ordering properties of columnar discotic triazines containing three pendant triphenylenes with four or five fluorinated tails. Liq Cryst. 2015;42(10):1450–1459.
  • Beltrán E, Serrano JL, Sierra T, et al. Tris(triazolyl)triazine via click-chemistry: a C3 electron-deficient core with liquid crystalline and luminescent properties. Org Lett. 2010;12:1404–1407.
  • Bhalla V, Singh H, Kumar M, et al. Triazole-modified triphenylene derivative: self-assembly and sensing applications. Langmuir. 2011;27(24):15275–15281.
  • Basak D, Christensen S, Surampudi SK, et al. Proton conduction in discotic mesogens. Chem Commun. 2011;47(19):5566–5568. .
  • Ryu MH, Choi JW, Cho BK. Design, synthesis, and self-assembly behavior of C3-symmetry discotic molecules via click chemistry. J Mater Chem. 2010;20(9):1806–1810.
  • Choi JW, Ryu MH, Lee E, et al. Ion-induced bicontinuous cubic and columnar liquid-crystalline assemblies of discotic block codendrimers. Chem Eur J. 2010;16(30):9006–9009. .
  • Beltran E, Serrano JL, Sierra T, et al. Functional star-shaped tris(triazolyl)triazines: columnar liquid crystal, fluorescent, solvatofluorochromic and electrochemical properties. J Mater Chem. 2012;22:7797–7805.
  • Nguyen ML, Kim HJ, Cho BK. Peripheral chain length-dependent complex phase behaviour in C3-symmetric hexa-alkylated liquid crystals. Liq Cryst. 2018;45(8):1196–1209.
  • Cho BK, Kim SH. Supramolecular transformation from ordered columnar to disordered columnar to tetragonal micellar structures in clicked dodeca-alkylated discotic triphenylene liquid crystals. Soft Matter. 2014;10(4):553–559.
  • Kim J, Cho S, Cho BK. An unusual stacking transformation in liquid-crystalline columnar assemblies of clicked molecular propellers with tunable light emissions. Chem Eur J. 2014;20(40):12734–12739.
  • Han K, Cho BK. Chain-dependent emission color codes of extended tetraphenylethylene derivatives: discrimination between water and methanol. RSC Adv. 2015;5(13):9510–9517.
  • Bui HT, Kim J, Kim HJ, et al. Advantages of mobile liquid-crystal phase of AIE luminogens for effective solid-state emission. J Phys Chem C. 2016;120(47):26695–26702. .
  • Feringán B, Romero P, Serrano JL, et al. H-bonded donor–acceptor units segregated in coaxial columnar assemblies: toward high mobility ambipolar organic semiconductors. J Am Chem Soc. 2016;138(38):12511–12518. .
  • Ryu MH, Choi JW, Kim HJ, et al. Complementary hydrogen bonding between a clicked C3-symmetric triazole derivative and carboxylic acids for columnar liquid-crystalline assemblies. Angew Chem Int Ed. 2011;50(25):5737–5740. .
  • Park S, Ryu MH, Shin TJ, et al. Smectic assemblies in C3-symmetric hexa-alkylated liquid crystals: transformation from smectogen to discogen via hydrogen bonding. Soft Matter. 2014;10(31):5804–5809.
  • Zhao KQ, Bai XY, Xiao B, et al. Star-shaped triphenylene discotic liquid crystalline oligomers and their hydrogen-bonded supramolecular complexes with simple acids. J Mater Chem C. 2015;3(44):11735–11746.
  • Krikorian M, Liu S, Swager TM. Columnar liquid crystallinity and mechanochromism in cationic platinum(II) complexes. J Am Chem Soc. 2014;136(8):2952–2955.
  • Geng H, Luo KJ, Cheng HM, et al. Novel columnar metallomesogens based on cationic platinum(ii) complexes without long peripheral chains. RSC Adv. 2017;7(19):11389–11393.
  • Schulze B, Schubert US. Beyond click chemistry - supramolecular interactions of 1,2,3-triazoles. Chem Soc Rev. 2014;43:2522–2571.
  • Schweinfurth D, Hettmanczyk L, Suntrup L, et al. Metal complexes of click-derived triazoles and mesoionic carbenes: electron transfer, photochemistry, magnetic bistability, and catalysis. Z Anorg Allg Chem. 2017;643(9):554–584.
  • Suijkerbuijk BM, Aerts BN, Dijkstra HP, et al. “Click” 1,2,3-triazoles as tunable ligands for late transition metal complexes. Dalton Trans. 2007:1273–1276.
  • Hua YR, Flood AH. Click chemistry generates privileged CH hydrogen-bonding triazoles: the latest addition to anion supramolecular chemistry. Chem Soc Rev. 2010;39(4):1262–1271.
  • Huang DS, Zhao PX, Astruc D. Catalysis by 1,2,3-triazole- and related transition-metal complexes. Coordin Chem Rev. 2014;272:145–165.
  • Becer CR, Hoogenboom R, Schubert US. Click chemistry beyond metal-catalyzed cycloaddition. Angew Chem Int Ed. 2009;48(27):4900–4908.
  • Mueller JO, Schmidt FG, Blinco JP, et al. Visible-light-induced click chemistry. Angew Chem Int Ed. 2015;54(35):10284–10288.
  • Arseneault M, Levesque I, Morin JF. Efficient and rapid divergent synthesis of ethylene oxide-containing dendrimers through catalyst-free click chemistry. Macromolecules. 2012;45(9):3687–3694.
  • Bai YF, Bao L, Hu P, et al. Copper-free click chemistry between azides and internal alkynes for triphenylene discotic liquid crystal trimer formation. Liq Cryst. 2013;40(1):97–105.
  • Zhang K, Bai YF, Feng C, et al. Synthesis and characterization of new H-shaped triphenylene discotic room-temperature liquid crystal tetramers by a copper-free click reaction. New J Chem. 2018;42(1):272–280.
  • Wang BQ, Wang XL, Zhao KQ, et al. Synthesis and mesomorphism of perfluoroalkyl chain containing biphenyl liquid crystals. Acta Chim Sin. 2007;65:2499–2504.
  • Badeche S, Daran JC, Ruiz J, et al. Synthesis and coordination chemistry of ferrocenyl-1,2,3-triazolyl ligands. Inorg Chem. 2008;47(11):4903–4908.
  • Keshav K, Singh N, Elias AJ. Synthesis and reactions of ethynylferrocene-derived fluoro- and chlorocyclotriphosphazenes. Inorg Chem. 2010;49(12):5753–5765.
  • Crowley JD, Gavey EL. Use of di-1,4-substituted-1,2,3-triazole “click” ligands to self-assemble dipalladium(ii) coordinatively saturated, quadruply stranded helicate cages. Dalton Trans. 2010;39(17):4035–4037.
  • Wang LL, Kiemle DJ, Boyle CJ, et al. “Click” synthesis of intrinsically hydrophilic dendrons and dendrimers containing metal binding moieties at each branching unit. Macromolecules. 2014;47(7):2199–2213. .
  • Xu HT, Xia X, Yu WH, et al. Effect of methoxy groups on liquid crystalline and self-assembling properties of 2,7,12-tris(methoxy)-3,8,13-tris(alkoxy)-5,10,15-truxenones. Liq Cryst. 2021;48(1):111–120. .
  • Zhao KQ, An LL, Zhang XB, et al. Highly segregated lamello-columnar mesophase organizations and fast charge carrier mobility in new discotic donor-acceptor triads. Chem Eur J. 2015;21(29):10379–10390. .
  • Ruan P, Xiao B, Ni HL, et al. The influence of alkyl chain substitution pattern on the two- and three-dimensional self-assembly of truxenone discogens. Liq Cryst. 2014;41(8):1152–1161. .
  • Sıdır İ, Sıdır YG, Kumalar M, et al. Ab initio Hartree–Fock and density functional theory investigations on the conformational stability, molecular structure and vibrational spectra of 7-acetoxy-6-(2,3-dibromopropyl)-4,8-dimethylcoumarin molecule. J Mol Struct. 2010;964(1–3):134–151.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.