{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T14:34:32Z","timestamp":1790778872766,"version":"4.1.0"},"reference-count":116,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2016,12,22]],"date-time":"2016-12-22T00:00:00Z","timestamp":1482364800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2017,2,16]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The formation of distinct supramolecular assemblies, including a metastable species, is revealed for a lipophilic guanosine (G) derivative in solution and in the solid state. Structurally different G\u2010quartet\u2010based assemblies are formed in chloroform depending on the nature of the cation, anion and the salt concentration, as characterized by circular dichroism and time course diffusion\u2010ordered NMR spectroscopy data. Intriguingly, even the presence of potassium ions that stabilize G\u2010quartets in chloroform was insufficient to exclusively retain such assemblies in the solid state, leading to the formation of mixed quartet and ribbon\u2010like assemblies as revealed by fast magic\u2010angle spinning (MAS) NMR spectroscopy. Distinct N\u2212H\u22c5\u22c5\u22c5N and N\u2212H\u22c5\u22c5\u22c5O intermolecular hydrogen bonding interactions drive quartet and ribbon\u2010like self\u2010assembly resulting in markedly different 2D <jats:sup>1<\/jats:sup>H solid\u2010state NMR spectra, thus facilitating a direct identification of mixed assemblies. A dissolution NMR experiment confirmed that the quartet and ribbon interconversion is reversible\u2013further demonstrating the changes that occur in the self\u2010assembly process of a lipophilic nucleoside upon a solid\u2010state to solution\u2010state transition and vice versa. A systematic study for complexation with different cations (K<jats:sup>+<\/jats:sup>, Sr<jats:sup>2+<\/jats:sup>) and anions (picrate, ethanoate and iodide) emphasizes that the existence of a stable solution or solid\u2010state structure may not reflect the stability of the same supramolecular entity in another phase.<\/jats:p>","DOI":"10.1002\/chem.201604832","type":"journal-article","created":{"date-parts":[[2016,11,29]],"date-time":"2016-11-29T08:59:15Z","timestamp":1480409955000},"page":"2315-2322","source":"Crossref","is-referenced-by-count":31,"title":["Co\u2010existence of Distinct Supramolecular Assemblies in Solution and in the Solid State"],"prefix":"10.1002","volume":"23","author":[{"given":"G. N. Manjunatha","family":"Reddy","sequence":"first","affiliation":[{"name":"Department of Physics and Department of Chemistry University of  Warwick, Coventry CV4 7AL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aida","family":"Huqi","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica \u201cGiacomo Ciamician\u201d, Alma Mater Studiorum Universit\u00e0 di Bologna  40126 Bologna Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dinu","family":"Iuga","sequence":"additional","affiliation":[{"name":"Department of Physics and Department of Chemistry University of  Warwick, Coventry CV4 7AL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Satoshi","family":"Sakurai","sequence":"additional","affiliation":[{"name":"JEOL (UK), Silver Court, Watchmead  Welwyn Garden City AL7 1LT UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrew","family":"Marsh","sequence":"additional","affiliation":[{"name":"Department of Physics and Department of Chemistry University of  Warwick, Coventry CV4 7AL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jeffery T.","family":"Davis","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Maryland  College Park MD 20742 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stefano","family":"Masiero","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica \u201cGiacomo Ciamician\u201d, Alma Mater Studiorum Universit\u00e0 di Bologna  40126 Bologna Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2069-8496","authenticated-orcid":false,"given":"Steven P.","family":"Brown","sequence":"additional","affiliation":[{"name":"Department of Physics and Department of Chemistry University of  Warwick, Coventry CV4 7AL UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,12,22]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1205962"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr3002824"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4NR01788A"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198800891"},{"key":"e_1_2_7_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19881000110"},{"key":"e_1_2_7_6_1","unstructured":"\u00a0"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature08165"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.290"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00299"},{"key":"e_1_2_7_10_1","unstructured":"\u00a0"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkn968"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja901574c"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.957"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201306230"},{"key":"e_1_2_7_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201306230"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja505101a"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00456"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00608"},{"key":"e_1_2_7_18_1","unstructured":"\u00a0"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.48.12.2013"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature755"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkl655"},{"key":"e_1_2_7_22_1","unstructured":"\u00a0"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature08403"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201001436"},{"key":"e_1_2_7_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201001436"},{"key":"e_1_2_7_25_1","unstructured":"\u00a0"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja904007p"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkr539"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0302174"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0340634"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470661345.smc026"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b02420"},{"key":"e_1_2_7_32_1","unstructured":"\u00a0"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrd3428"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15067g"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500891"},{"key":"e_1_2_7_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201500891"},{"key":"e_1_2_7_36_1","unstructured":"\u00a0"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300589"},{"key":"e_1_2_7_37_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300589"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/B600282J"},{"key":"e_1_2_7_39_1","unstructured":"\u00a0"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0501663102"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja507506c"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b02753"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00183A"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702605"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200702605"},{"key":"e_1_2_7_45_1","unstructured":"\u00a0"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00116a011"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00124a003"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/23.4.696"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.1476700"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1038\/nnano.2014.246"},{"key":"e_1_2_7_51_1","unstructured":"\u00a0"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja970248x"},{"key":"e_1_2_7_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9925148"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja056888e"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja058157k"},{"key":"e_1_2_7_56_1","unstructured":"\u00a0"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0455650"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1039\/b505674h"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.12.100"},{"key":"e_1_2_7_60_1","unstructured":"\u00a0"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja035267n"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol061115w"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja064878n"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc14965b"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.177"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b01113"},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(20000403)39:7<1300::AID-ANIE1300>3.0.CO;2-I"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(20000403)112:7<1356::AID-ANGE1356>3.0.CO;2-V"},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.11.005"},{"key":"e_1_2_7_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol006916s"},{"key":"e_1_2_7_70_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.64.685"},{"key":"e_1_2_7_71_1","unstructured":"\u00a0"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1006\/jmra.1995.1068"},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1006\/jmre.1998.1432"},{"key":"e_1_2_7_74_1","unstructured":"\u00a0"},{"key":"e_1_2_7_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200400782"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200601461"},{"key":"e_1_2_7_77_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200601015"},{"key":"e_1_2_7_78_1","unstructured":"\u00a0"},{"key":"e_1_2_7_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr990132e"},{"key":"e_1_2_7_80_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.pnmrs.2006.10.002"},{"key":"e_1_2_7_81_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ssnmr.2011.11.006"},{"key":"e_1_2_7_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500518"},{"key":"e_1_2_7_82_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201500518"},{"key":"e_1_2_7_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemmater.5b00360"},{"key":"e_1_2_7_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.5b00279"},{"key":"e_1_2_7_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00258"},{"key":"e_1_2_7_86_1","unstructured":"\u00a0"},{"key":"e_1_2_7_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja206516u"},{"key":"e_1_2_7_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.5b01440"},{"key":"e_1_2_7_89_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ssnmr.2015.01.001"},{"key":"e_1_2_7_90_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199307031"},{"key":"e_1_2_7_90_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19931050525"},{"key":"e_1_2_7_91_1","unstructured":"\u00a0"},{"key":"e_1_2_7_92_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905827"},{"key":"e_1_2_7_92_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200905827"},{"key":"e_1_2_7_93_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201000805"},{"key":"e_1_2_7_93_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201000805"},{"key":"e_1_2_7_94_2","first-page":"28","volume-title":"Self-Assembly of Lipophilic Guanosines: Switching between Different Assemblies","author":"Masiero S.","year":"2013"},{"key":"e_1_2_7_95_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201209616"},{"key":"e_1_2_7_95_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201209616"},{"key":"e_1_2_7_96_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201404266"},{"key":"e_1_2_7_96_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201404266"},{"key":"e_1_2_7_97_1","unstructured":"\u00a0"},{"key":"e_1_2_7_98_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352641"},{"key":"e_1_2_7_98_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200352641"},{"key":"e_1_2_7_99_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200704535"},{"key":"e_1_2_7_99_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200704535"},{"key":"e_1_2_7_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja307231u"},{"key":"e_1_2_7_101_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC03197D"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201604832","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201604832","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T09:02:12Z","timestamp":1760259732000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201604832"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,12,22]]},"references-count":116,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2017,2,16]]}},"alternative-id":["10.1002\/chem.201604832"],"URL":"https:\/\/doi.org\/10.1002\/chem.201604832","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,12,22]]}}}