Abstract
Anthracene-based cylindrical macrotricyclic polyether (1) containing two dibenzo-30-crown-10 cavities has been proved to be an efficient host for the templated complexation with N,N′-dipropyl-1,4,5,8-naphthalenetetracarboxylic diimide in the presence of lithium ions in both solution and solid state. Host 1 could also form 1:1 complex with the bispyridinium salt with two β-hydroxyethyl groups in solution and in the solid state. Moreover, it was also found that the switchable complexation processes between the macrotricyclic host and two different kinds of guests could be chemically controlled by the addition and removal of lithium ions.
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Feringa BL. Molecular Switches. Germany Weinheim: Wiley-VCH Verlag GmbH, 2001
Balzani V, Credi A, Venturi M. Molecular Devices and Machines: Concepts and Perspectives for the Nanoworld. Germany Weinheim: Wiley-VCH Verlag GmbH, 2008
Saha S, Stoddart JF. Photo-driven molecular devices. Chem Soc Rev, 2007, 36: 77–92
Kinbara K, Aida T. Toward intelligent molecular machines: Directed motions of biological and artificial molecules and assemblies. Chem Rev, 2005, 105: 1377–1400
Tian H, Wang QC. Recent progress on switchable rotaxanes. Chem Soc Rev, 2006, 35: 361–374
Kay ER, Leigh DA, Zerbetto F. Synthetic molecular motors and mechanical machines. Angew Chem Int Ed, 2007, 46: 72–191
Green JE, Wook Choi J, Boukai A, Bunimovich Y, Johnston-Halperin E, Deionno E, Luo Y, Sheriff BA, Xu K, Shik Shin Y, Tseng H-R, Green JE, Wook Choi J, Boukai A, Bunimovich Y, Johnston-Halperin E, Deionno E, Luo Y, Sheriff BA, Xu K, Shik Shin Y, Tseng H-R, Stoddart JF, Heath JR. A 160-kilobit molecular electronic memory patterned at 1011 bits per square centimeter. Nature, 2007, 445: 414–417
Nakanishi H, Walker DA, Bishop KJM, Wesson PJ, Yan Y, Soh S, Swaminathan S, Grzybowski BA. Dynamic internal gradients control and direct electric currents within nanostructured materials. Nat Nanotech, 2011, 6: 740–746
Banerjee IA, Yu L, Matsui H. Application of host-guest chemistry in nanotube-based device fabrication: Photochemically controlled immobilization of azobenzene nanotubes on patterned α-CD monolayer/Au substrates via molecular recognition. J Am Chem Soc, 2003, 125: 9542–9543
Shinkai S. Switch-functionalized systems in biomimetic chemistry. Pure Appl Chem, 1987, 59: 425–430
Shinkai S. Photoresponsive crown ethers. 2. Photocontrol of ion extraction and ion transport by a bis(crown ether) with a butterfly-like motion. J Am Chem Soc, 1981, 103: 111–115
Dohno C, Nakatani K. Control of DNA hybridization by photoswitchable molecular glue. Chem Soc Rev, 2011, 40: 5718–5729
Merino E. Synthesis of azobenzenes: The coloured pieces of molecular materials. Chem Soc Rev, 2011, 40: 3835–3853
Mohideen IH, Xiao B, Wheatley PS, McKinlay AC, Li Y, Slawin AMZ, Aldous DW, Cessford NF, Düren T, Zhao XB, Gill R, Thomas KM, Griffin JM, Ashbrook SE, Morris RE. Protecting group and switchable pore-discriminating adsorption properties of a hydrophilichydrophobic metal-organic framework. Nat Chem, 2011, 3: 304–310
Wang JB, Feringa BL. Dynamic control of chiral space in a catalytic asymmetric reaction using a molecular motor. Science, 2011, 331: 1429–1432
Serreli V, Lee CF, Kay ER, Leigh DA. A molecular information ratchet. Nature, 2007, 445: 523–527
Collier CP, Mattersteig G, Wong EW, Luo Y, Beverly K, Sampaio J, Raymo FM, Stoddart JF, Heath JR. A [2]catenane based solid-state electronically reconfigurable switch. Science, 2000, 289: 1172–1175
Zhao YL, Dichtel WR, Trabolsi A, Saha S, Aprahamian I, Stoddart JF. A redox-switchable α-cyclodextrin-based [2]rotaxane. J Am Chem Soc, 2008, 130: 11294–11296
Zhao YL, Aprahamian I, Trabolsi A, Erina N, Stoddart JF. Organogel formation by a cholesterol-stoppered bistable [2]rotaxane and its dumbbell precursor. J Am Chem Soc, 2008, 130: 6348–6350
Steuerman DW, Tseng H-R, Peters AJ, Flood AH, Jeppesen JO, Nielsen KA, Stoddart JF, Heath JR. Molecular-mechanical switchbased solid-state electrochromic devices. Angew Chem Int Ed, 2004, 43: 6486–6491
Sindelar V, Silvi S, Kaifer AE. Switching a molecular shuttle on and off: simple, pH-controlled pseudorotaxanes based on cucurbit[7]uril. Chem Commun, 2006, 20: 2185–2187
Ooya T, Inoue D, Choi HS, Kobayashi Y, Loethen S, Thompson DH, Ko YH, Kim K, Yui N. PH-responsive movement of cucurbit[7]uril in a diblock polypseudorotaxane containing dimethyl β-cyclodextrin and cucurbit[7]uril. Org Lett, 2006, 8: 3159–3162
Sobransingh D, Kaifer AE. Electrochemically switchable cucurbit [7]uril-based pseudorotaxanes. Org Lett, 2006, 8: 3247–3250
Tuncel D, Xzsar X, Tiftik HB, Salih B. Molecular switch based on a cucurbit[6]uril containing bistable [3]rotaxane. Chem Commun, 2007, 13: 1369–1371
Chakrabarti S, Mukhopadhyay P, Lin S, Isaacs L. Reconfigurable four-component molecular switch based on pH-controlled guest swapping. Org Lett, 2007, 9: 2349–2352
Liu Y, Li XY, Zhang HY, Li CJ, Ding F. Cyclodextrin-driven movement of cucurbit[7]uril. J Org Chem, 2007, 72: 3640–3645
An H, Bradshaw J S, Izatt R M. Macropolycyclic polyethers (cages) and related compounds. Chem Rev, 1992, 92: 543–572
Fages F, Desvergne J P, Kampke K, Bouas-Laurent H, Lehn JM, Meyer M, Albrecht-Gary AM. Linear molecular recognition: Spectroscopic, photophysical, and complexation studies on alpha, omegaalkanediyldiammonium ions binding to a bisanthracenyl macrotricyclic receptor. J Am Chem Soc, 1993, 115: 3658–3664
Huang F, Zakharov LN, Rheingold AL, Ashraf-Khorassani M, Gibson HW. Synthesis of a symmetric cylindrical Bis(crown ether) host and its complexation with paraquat. J Org Chem, 2005, 70: 809–813
Huang F, Gibson H W. A supramolecular poly[3]pseudorotaxane by self-assembly of a homoditopic cylindrical bis(crown ether) host and a bisparaquat derivative. Chem Commun, 2005, (13): 1696–1698
Zong QS, Chen CF. Novel triptycene-based cylindrical macrotricyclic host: Synthesis and complexation with paraquat derivatives. Org Lett, 2006, 8: 211–214
Zhao JM, Zong QS, Han T, Xiang JF, Chen CF. Guest-dependent complexation of triptycene-based macrotricyclic host with paraquat derivatives and secondary ammonium salts: A chemically controlled complexation process. J Org Chem, 2008, 73: 6800–6806
Han T, Chen CF. Formation of ternary complexes between a macrotricyclic host and hetero-guest pairs: An acid-base controlled selective complexation process. Org Lett, 2007, 9: 4207–4210
Han T, Chen CF. Efficient potassium-ion-templated synthesis and controlled destruction of [2]rotaxanes based on cascade complexes. J Org Chem, 2008, 73: 7735–7742
Han T, Chen CF. Selective templated complexation of a cylindrical macrotricyclic host with neutral guests: Three cation-controlled switchable processes. J Org Chem, 2007, 72: 7287–7293
Zong QS, Zhang C, Chen CF. Self-assembly of triptycene-based cylindrical macrotricyclic host with dibenzylammonium ions: Construction of dendritic [3]pseudorotaxanes. Org Lett, 2006, 8: 1859–1862
Su YS, Chen CF. Novel anthracene-based cylindrical macrotricyclic polyether: Powerful host for bispyridinium dications. Org Lett, 2010, 12: 1888–1891
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Zeng, F., Su, Y. & Chen, C. Li+-templated complexation of cylindrical macrotricyclic host with naphthalene diimide: Cation-controlled switchable complexation processes. Sci. China Chem. 55, 2069–2074 (2012). https://doi.org/10.1007/s11426-012-4671-1
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DOI: https://doi.org/10.1007/s11426-012-4671-1