Polymerizable channel-like stacks derived from cyclic tetrameric diacetylenes

Ryu, 2005, Tubular assembly of amphiphilic rigid macrocycle with flexible dendrons, Chem. Commun., 1770, 10.1039/b419213c Zhong, 2017, Enforced tubular assembly of electronically different hexakis(m-phenylene ethynylene) macrocycles: persistent columnar stacking driven by multiple hydrogen-bonding interactions, J. Am. Chem. Soc., 139, 15950, 10.1021/jacs.7b09647 Petryk, 2017, Unexpected formation of a tubular architecture by optically active pure organic calixsalen, CrystEngComm, 19, 5825, 10.1039/C7CE01529A Zhen, 2018, Acid-responsive conductive nanofiber of tetrabenzoporphyrin made by solution processing, J. Am. Chem. Soc., 140, 62, 10.1021/jacs.7b10575 Wang, 2020, Self-Assembly and molecular recognition in water: tubular stacking and guest-templated discrete assembly of water-soluble, shape-persistent macrocycles, J. Am. Chem. Soc., 142, 2915, 10.1021/jacs.9b11536 Schneebeli, 2013, Asararenes—a family of large aromatic macrocycles, Chem. Eur J., 19, 3860, 10.1002/chem.201204097 Negin, 2011, Pore formation in phospholipid bilayers by branched-chain pyrogallol[4]arenes, J. Am. Chem. Soc., 133, 3234, 10.1021/ja1085645 Kumari, 2012, Investigating structural alterations in pyrogallol[4]arene-pyrene nanotubular frameworks, Small, 8, 3321, 10.1002/smll.201201384 Matsubara, 2019, Phototriggered dynamic and biomimetic growth of chlorosomal self-aggregates, J. Am. Chem. Soc., 141, 1207, 10.1021/jacs.8b13056 Mossine, 2012, Ferrocene species included within a pyrogallol[4]arene Tube, Chem. Eur J., 18, 10258, 10.1002/chem.201200263 Suzuki, 2016, Directing the crystallization of dehydro[24]annulenes into supramolecular nanotubular scaffolds, J. Am. Chem. Soc., 138, 5939, 10.1021/jacs.6b01939 DeHaven, 2019, Probing the formation of reactive oxygen species by a porous self-assembled benzophenone bis-urea host, ACS Omega, 4, 8290, 10.1021/acsomega.9b00831 Tahir, 2018, Recent progress in the stabilization of supramolecular assemblies with functional polydiacetylenes, Polym. Chem., 9, 3019, 10.1039/C8PY00536B Lapini, 2018, Topochemical polymerization of phenylacetylene macrocycles under pressure, J. Phys. Chem. C, 122, 20034, 10.1021/acs.jpcc.8b06724 Chance, 1977, An examination of the thermal polymerization of a crystalline diacetylene using diffuse reflectance spectroscopy, J. Am. Chem. Soc., 99, 6703, 10.1021/ja00462a038 Tang, 2020, Fabrication of polydiacetylene particles using a solvent injection method, Mater. Adv., 1, 1745, 10.1039/D0MA00442A Pham, 2020, Visual simultaneous detection and real-time monitoring of cadmium ions based on conjugated polydiacetylenes, ACS Omega, 5, 31254, 10.1021/acsomega.0c04636 Shin, 2020, Protonation-triggered supramolecular gel from macrocyclic diacetylene: gelation behavior, topochemical polymerization, and colorimetric response, Langmuir, 36, 13971, 10.1021/acs.langmuir.0c02469 Krishnan, 2016, Organogel-assisted topochemical synthesis of multivalent glyco-polymer for high-affinity lectin binding, Chem. Commun., 52, 14089, 10.1039/C6CC07993H Weston, 2021, Digital analysis of polydiacetylene quality tags for contactless monitoring of milk, Anal. Chim. Acta, 1148, 10.1016/j.aca.2020.12.065 Kim, 2021, Polydiacetylenes containing 2-picolylamide chemosensor for colorimetric detection of cadmium ions, Bull. Kor. Chem. Soc., 42, 265, 10.1002/bkcs.12163 Liang, 2012, Electromechanical actuator with controllable motion, fast response rate, and high-frequency resonance based on graphene and polydiacetylene, ACS Nano, 6, 4508, 10.1021/nn3006812 Tian, 2020, Polydiacetylene-based ultrastrong bioorthogonal Raman probes for targeted live-cell Raman imaging, Nat. Commun., 11, 81, 10.1038/s41467-019-13784-0 Huang, 2020, Highly sensitive polydiacetylene ensembles for biosensing and bioimaging, Front. Chem., 8, 10.3389/fchem.2020.565782 Tahir, 2019, Topochemical polymerization of a nematic tetraazaporphyrin derivative to generate soluble polydiacetylene nanowires, Langmuir, 35, 15158, 10.1021/acs.langmuir.9b02187 Kim, 2018, Tuning of the topochemical polymerization of diacetylenes based on an odd/even effect of the peripheral alkyl chain: thermochromic reversibility in a thin film and a single-component ink for a fountain pen, ACS Appl. Mater. Interfaces, 10, 24767, 10.1021/acsami.8b05896 Jordan, 2016, Synthesis of graphene nanoribbons via the topochemical polymerization and subsequent aromatization of a diacetylene precursor, Inside Chem., 1, 78 Baughman, 1975, Cyclically-bound ladder polymers of cyclic diacetylene tetramers, US Patent, 3 Baughman, 2004, Topochemical strategies and experimental results for the rational synthesis of carbon nanotubes of one specified type, Synth. Met., 141, 87, 10.1016/j.synthmet.2003.09.025 Xu, 2010, Thermal reaction of a columnar assembled diacetylene macrocycle, J. Am. Chem. Soc., 132, 5334, 10.1021/ja9107066 Shin, 2020, Protonation-induced self-assembly of flexible macrocyclic diacetylene for constructing stimuli-responsive polydiacetylene, Macromolecules, 53, 149, 10.1021/acs.macromol.9b02133 Heo, 2017, Chromogenic tubular polydiacetylenes from topochemical polymerization of self-assembled macrocyclic diacetylenes, Macromolecules, 50, 900, 10.1021/acs.macromol.6b02493 Shin, 2019, Cation-directed self-assembly of macrocyclic diacetylene for developing chromogenic polydiacetylene, ACS Macro Lett., 8, 610, 10.1021/acsmacrolett.9b00169 Sondheimer, 1959, Unsaturated macrocyclic compounds. VIII.1 Oxidation of terminal diacetylenes to large ring polyacetylenes with cupric acetate in pyridine. Synthesis of five new macrocyclic rings, J. Am. Chem. Soc., 81, 4600, 10.1021/ja01526a038 Banerjie, 1979, Characterization of the ladder polymerization of a crystalline cyclotetradiyne monomer, J. Polymer Sci., Polymer Phys., 17, 655, 10.1002/pol.1979.180170408 Yee, 1979, Solid-state synthesis of a ladder polymer, J. Polymer Sci. Polymer Chem., 17, 3637, 10.1002/pol.1979.170171119 Xu, 2014, Single crystal to single crystal polymerization of a self-assembled diacetylene macrocycle affords columnar polydiacetylenes, Cryst. Growth Des., 14, 993, 10.1021/cg401380a Kantha, 2018, Topochemical polymerization of macrocyclic diacetylene with a naphthalene moiety for a tubular-shaped polydiacetylene chromophore, Dyes Pigments, 154, 199, 10.1016/j.dyepig.2018.02.039 Bae, 2020, Macrocyclic diacetylene–terthiophene cocrystal: molecular self-assembly, topochemical polymerization, and energy transfer, Cryst. Growth Des., 20, 434, 10.1021/acs.cgd.9b01351 Nagasawa, 2011, Synthesis, gelation properties and photopolymerization of macrocyclic diacetylenedicarboxamides derived from L-glutamic acid and trans-1,4-cyclohexanediol, Eur. J. Org Chem., 12, 2247, 10.1002/ejoc.201001533 Heo, 2019, Thermochromic polydiacetylene nanotube from amphiphilic macrocyclic diacetylene in aqueous solution, Macromolecules, 52, 4405, 10.1021/acs.macromol.9b00635 As a matter of fact, diffusion NMR (DECRA analysis, DMSO-d6) as well as GPC (DMF) data did not provide sufficient evidence for polymerization induced by UV-light (UV-254 nm lamp or LED UV, 3 days) as well as by thermal annealing (120 °C, 12 hr) due to mostly insoluble nature of polymer. GPC showed no integrable peaks in polymerized DA-4 samples or exhibited very low intensity peaks with number average molecular weight (Mn) ∼ 1.9 kDa. Maeda, 2014, Chiral amplification in polymer brushes consisting of dynamic helical polymer chains through the long-range communication of stereochemical information, Macromolecules, 47, 6540, 10.1021/ma501612e Ohsawa, 2011, Hierarchical amplification of macromolecular helicity of dynamic helical poly(phenylacetylene)s composed of chiral and achiral phenylacetylenes in dilute solution, liquid crystal, and two-dimensional crystal, J. Am. Chem. Soc., 133, 108, 10.1021/ja1087453 Yang, 2019, The chirality induction and modulation of polymers by circularly polarized light, Symmetry, 11, 474, 10.3390/sym11040474 Chen, 2016, Fabrication of helical nanoribbon polydiacetylene via supramolecular gelation: circularly polarized luminescence and novel diagnostic chiroptical signals for sensing, ACS Appl. Mater. Interfaces, 8, 30608, 10.1021/acsami.6b10392 Li, 2017, Self-assembled polydiacetylene vesicle and helix with chiral interface for visualized enantioselective recognition of sulfinamide, ACS Appl. Mater. Interfaces, 9, 37386, 10.1021/acsami.7b10353 Rosenthal, 2011, On the nature of chirality imparted to achiral polymers by the crystallization process, Angew. Chem. Int. Ed., 50, 8881, 10.1002/anie.201102814 Sheldrick, 2008, A short history of SHELX, Acta Crystallogr., A64, 112, 10.1107/S0108767307043930 Bruker, 2005 Dolomanov, 2009, OLEX2: a complete structure solution, refinement and analysis program, J. Appl. Crystallogr., 42, 339, 10.1107/S0021889808042726 2018