{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T19:36:49Z","timestamp":1789587409912,"version":"build-2803163510"},"reference-count":95,"publisher":"Wiley","issue":"22","license":[{"start":{"date-parts":[[2017,2,16]],"date-time":"2017-02-16T00:00:00Z","timestamp":1487203200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["26102001"],"award-info":[{"award-number":["26102001"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["26102010"],"award-info":[{"award-number":["26102010"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["26\u00b77715"],"award-info":[{"award-number":["26\u00b77715"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2017,4,19]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Intricately designed \u03c0\u2010conjugated molecules containing interactive groups can be used to generate supramolecular polymers with outstanding structural and functional properties. To construct such supramolecular polymers, the non\u2010covalent synthesis of supermacrocyclic monomers from relatively simple molecules represents an attractive strategy, although this has been rarely exploited. Here, we report the supramolecular polymerization of two barbiturate\u2010naphthalene derivatives that circularly hexamerize by hydrogen bonding. The two molecules contain an aliphatic \u201cwedge\u201d unit with either an ether or ester linkage. This subtle difference is amplified into distinct features both in terms of the morphology of the supramolecular polymers and the polymerization process. The degrees of conformational freedom of the wedge unit determine the stacking of the supermacrocycles, as is evident from 2D X\u2010ray diffraction analyses on the aligned fibers. The differences in stacking impart the supramolecular polymer fibers with different morphological features (cylindrical or helical), which are reflected in the properties of concentrated solutions (suspension or gel). The degrees of conformational freedom of the wedge unit also affect the polymerization kinetics, in which the more flexible ether linkage induces pathway complexity by the formation of off\u2010pathway aggregates.<\/jats:p>","DOI":"10.1002\/chem.201605873","type":"journal-article","created":{"date-parts":[[2017,1,25]],"date-time":"2017-01-25T04:46:50Z","timestamp":1485319610000},"page":"5270-5280","source":"Crossref","is-referenced-by-count":31,"title":["Supramolecular Polymerization of Supermacrocycles: Effect of Molecular Conformations on Kinetics and Morphology"],"prefix":"10.1002","volume":"23","author":[{"given":"Mitsuaki","family":"Yamauchi","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry and Biotechnology, Graduate School of Engineering Chiba University  1\u201333 Yayoi-cho, Inage-ku Chiba 263-8522 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bimalendu","family":"Adhikari","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry and Biotechnology, Graduate School of Engineering Chiba University  1\u201333 Yayoi-cho, Inage-ku Chiba 263-8522 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Deepak D.","family":"Prabhu","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry and Biotechnology, Graduate School of Engineering Chiba University  1\u201333 Yayoi-cho, Inage-ku Chiba 263-8522 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xu","family":"Lin","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry and Biotechnology, Graduate School of Engineering Chiba University  1\u201333 Yayoi-cho, Inage-ku Chiba 263-8522 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takashi","family":"Karatsu","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry and Biotechnology, Graduate School of Engineering Chiba University  1\u201333 Yayoi-cho, Inage-ku Chiba 263-8522 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomonori","family":"Ohba","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Science Chiba University  1\u201333 Yayoi-cho, Inage-ku Chiba 263-8522 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nobutaka","family":"Shimizu","sequence":"additional","affiliation":[{"name":"Photon Factory, Institute of Materials Structure Science High Energy Accelerator Research Organization  1-1, Oho Tsukuba 305-0801 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hideaki","family":"Takagi","sequence":"additional","affiliation":[{"name":"Photon Factory, Institute of Materials Structure Science High Energy Accelerator Research Organization  1-1, Oho Tsukuba 305-0801 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rie","family":"Haruki","sequence":"additional","affiliation":[{"name":"Photon Factory, Institute of Materials Structure Science High Energy Accelerator Research Organization  1-1, Oho Tsukuba 305-0801 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shin\u2010ichi","family":"Adachi","sequence":"additional","affiliation":[{"name":"Photon Factory, Institute of Materials Structure Science High Energy Accelerator Research Organization  1-1, Oho Tsukuba 305-0801 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takashi","family":"Kajitani","sequence":"additional","affiliation":[{"name":"Laboratory for Chemistry and Life Science, Institute of Innovative Research Tokyo Institute of Technology  4259 Nagatsuta, Midori-ku Yokohama 226\u20138503 Japan"},{"name":"RIKEN SPring-8 Center  1-1-1 Kouto, Sayo Hyogo 679\u20135148 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takanori","family":"Fukushima","sequence":"additional","affiliation":[{"name":"Laboratory for Chemistry and Life Science, Institute of Innovative Research Tokyo Institute of Technology  4259 Nagatsuta, Midori-ku Yokohama 226\u20138503 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shiki","family":"Yagai","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry and Biotechnology, Graduate School of Engineering Chiba University  1\u201333 Yayoi-cho, Inage-ku Chiba 263-8522 Japan"},{"name":"Molecular Chirality Research Center Chiba University  1\u201333 Yayoi-cho, Inage-ku Chiba 263\u20138522 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,2,16]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198305653"},{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19830950803"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/2171053a0"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M111402200"},{"key":"e_1_2_6_4_1","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030070z"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/B809359H"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr400195e"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.20140261"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00497C"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CE01968D"},{"key":"e_1_2_6_11_1","unstructured":"\u00a0"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1127884"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja900684h"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200902415"},{"key":"e_1_2_6_15_1","unstructured":"\u00a0"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2836(62)80112-0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-3495(86)83498-1"},{"key":"e_1_2_6_18_1","unstructured":"\u00a0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201003419"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja204811b"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature10720"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1849"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm4021172"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.6b00009"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2383"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr960037v"},{"key":"e_1_2_6_27_1","unstructured":"\u00a0"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/B308788C"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900181u"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1205962"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199622041"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19961081908"},{"key":"e_1_2_6_32_1","unstructured":"\u00a0"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00128a027"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja005886l"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja026164s"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352790"},{"key":"e_1_2_6_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200352790"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja052645a"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0706192"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201300025"},{"key":"e_1_2_6_40_1","unstructured":"\u00a0"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9005892"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200901336"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201102982"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201201436"},{"key":"e_1_2_6_44_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201201436"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603370"},{"key":"e_1_2_6_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201603370"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr900157q"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201006117"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201006117"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800417"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200800417"},{"key":"e_1_2_6_49_1","unstructured":"\u00a0"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00057a015"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0690(200005)2000:9<1727::AID-EJOC1727>3.0.CO;2-0"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201205504"},{"key":"e_1_2_6_52_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201205504"},{"key":"e_1_2_6_53_1","unstructured":"For2 the VPO measurement at 450\u2005mmrevealedN\u22484 which is different from the case of1(N=6); this difference is presumably due to increase of viscosity at higher concentrations (Figure\u2005S2 in the Supporting Information)."},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501321"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201501321"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac196511030371"},{"key":"e_1_2_6_56_1","unstructured":"\u00a0"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200602286"},{"key":"e_1_2_6_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200602286"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201602592"},{"key":"e_1_2_6_59_1","unstructured":"Even at 293\u2005K 1and2are weakly emissive in THF (Figure\u2005S6).[13d]."},{"key":"e_1_2_6_60_1","unstructured":"This quantum yield is relative to the fluorescence of a previously reported compound; for details see ref.\u2005[13d]."},{"key":"e_1_2_6_61_1","unstructured":"These peaks were assigned based on the XRD data of a bulk sample of1(Figure\u2005S15)."},{"key":"e_1_2_6_62_1","unstructured":"\u00a0"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja806524m"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja801179e"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200902416"},{"key":"e_1_2_6_66_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0365110X52001635"},{"key":"e_1_2_6_67_1","unstructured":"The pitch (P) of the sextuple-helix columns was estimated based on the following equation:P\/6=d\/cos\u03c6 wheredand\u03c6are thed-spacing (1: 1.05\u2005nm;2: 1.07\u2005nm) and the tilt angle (1: 51\u00b0;2: 54\u00b0) respectively."},{"key":"e_1_2_6_68_1","unstructured":"The values of\u03b1were calculated by normalization of the absorption change at a specific wavelength (1: 441\u2005nm;2: 460\u2005nm)."},{"key":"e_1_2_6_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja511952c"},{"key":"e_1_2_6_70_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201204556"},{"key":"e_1_2_6_71_1","unstructured":"As the absorption of the quenched solution of1is inconsistent with that of the monomer solution (c=3\u2005\u03bcm) at 293\u2005K 1should be kinetically trapped to form metastable \u03c0-\u03c0-stacked species (Figures\u20057\u2009a and S18)."},{"key":"e_1_2_6_72_1","unstructured":"Compared toSP1formed upon very slow cooling (\u0394T\/t=0.1\u2005K\u2009min\u22121; Figure\u2005S21) shorterSP1polymers were formed upon quenching; this is most likely due to a higher nucleation frequency which would explain the observed agglomeration upon drying."},{"key":"e_1_2_6_73_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1359-0278(96)00003-X"},{"key":"e_1_2_6_74_1","unstructured":"\u00a0"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1038\/357057a0"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp992338p"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200704550"},{"key":"e_1_2_6_77_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200704550"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1182767"},{"key":"e_1_2_6_79_1","unstructured":"\u00a0"},{"key":"e_1_2_6_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00032a007"},{"key":"e_1_2_6_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja104750f"},{"key":"e_1_2_6_82_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201404428"},{"key":"e_1_2_6_83_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja075987k"},{"key":"e_1_2_6_84_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b00504"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201605873","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201605873","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T13:48:48Z","timestamp":1760276928000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201605873"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,2,16]]},"references-count":95,"journal-issue":{"issue":"22","published-print":{"date-parts":[[2017,4,19]]}},"alternative-id":["10.1002\/chem.201605873"],"URL":"https:\/\/doi.org\/10.1002\/chem.201605873","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,2,16]]}}}