{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,5]],"date-time":"2026-04-05T07:46:44Z","timestamp":1775375204437,"version":"3.50.1"},"reference-count":72,"publisher":"Wiley","issue":"45","license":[{"start":{"date-parts":[[2018,7,11]],"date-time":"2018-07-11T00:00:00Z","timestamp":1531267200000},"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":["15H00954"],"award-info":[{"award-number":["15H00954"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2018,8,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Nitronyl nitroxide (NN)\u2010substituted conjugated oligomers, which were expected to self\u2010associate in biradical cation states, were designed to analyze the capability of \u03c0\u2010dimers as molecular wires. The oligomer moieties were composed of dithienyl\u2010<jats:italic>N<\/jats:italic>\u2010methylpyrrole with methoxy substituents at the inner \u03b2\u2010position of thiophene rings (DTP\u2010NN<jats:sup>.<\/jats:sup>) and its propylenedioxythiophene (ProDOT) inserted derivative (DTP\u2010P\u2010NN<jats:sup>.<\/jats:sup>), or two ethylenedioxythiophene (EDOT) and two ProDOT units (E<jats:sub>2<\/jats:sub>P<jats:sub>2<\/jats:sub>\u2010NN<jats:sup>.<\/jats:sup>). Among them, chemical one\u2010electron oxidation gave biradical cations (DTP\u2010P)<jats:sup>.+<\/jats:sup>\u2010NN<jats:sup>.<\/jats:sup> and (E<jats:sub>2<\/jats:sub>P<jats:sub>2<\/jats:sub>)<jats:sup>.+<\/jats:sup>\u2010NN<jats:sup>.<\/jats:sup> that formed \u03c0\u2010dimers (DTP\u2010P\u2010NN<jats:sup>.<\/jats:sup>)<jats:sub>2<\/jats:sub><jats:sup>2+<\/jats:sup> and (E<jats:sub>2<\/jats:sub>P<jats:sub>2<\/jats:sub>\u2010NN<jats:sup>.<\/jats:sup>)<jats:sub>2<\/jats:sub><jats:sup>2+<\/jats:sup> in dichloromethane at low temperatures. ESR studies of (DTP\u2010P\u2010NN<jats:sup>.<\/jats:sup>)<jats:sub>2<\/jats:sub><jats:sup>2+<\/jats:sup> and (E<jats:sub>2<\/jats:sub>P<jats:sub>2<\/jats:sub>\u2010NN<jats:sup>.<\/jats:sup>)<jats:sub>2<\/jats:sub><jats:sup>2+<\/jats:sup> showed the presence of a relatively strong exchange interaction between two NN radicals through the radical cation \u03c0\u2010dimer moieties. DFT calculations supported these experimental results and predicted that exchange interactions between two NN radicals were comparable or stronger than those through covalently linked quaterthiophene. Thus, the conjugated oligomer radical cation \u03c0\u2010dimers acted as efficient molecular wires for electronic communication.<\/jats:p>","DOI":"10.1002\/chem.201801712","type":"journal-article","created":{"date-parts":[[2018,5,24]],"date-time":"2018-05-24T08:39:43Z","timestamp":1527151183000},"page":"11717-11728","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Radical Cation \u03c0\u2010Dimers of Conjugated Oligomers as Molecular Wires: An Analysis Based on Nitronyl Nitroxide Spin Labels"],"prefix":"10.1002","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9081-3659","authenticated-orcid":false,"given":"Tohru","family":"Nishinaga","sequence":"first","affiliation":[{"name":"Department of Chemistry Graduate School of Science Tokyo Metropolitan University  Hachioji Tokyo 192-0397 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuki","family":"Kanzaki","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Osaka City University  Sumiyoshi-ku Osaka 558-8585 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Daisuke","family":"Shiomi","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Osaka City University  Sumiyoshi-ku Osaka 558-8585 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kenji","family":"Matsuda","sequence":"additional","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura Nishikyo-ku Kyoto, 615-8510 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shuichi","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Osaka City University  Sumiyoshi-ku Osaka 558-8585 Japan"},{"name":"Present Address: Division of Chemistry Graduate School of Engineering Science Osaka University  Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Keiji","family":"Okada","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Osaka City University  Sumiyoshi-ku Osaka 558-8585 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,7,11]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS90010G"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527633074"},{"key":"e_1_2_6_3_1","volume-title":"Molecular Wires","author":"de Cola L.","year":"2005"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/nnano.2006.130"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0500075102"},{"key":"e_1_2_6_6_1","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1002\/9781118858981.ch7","volume-title":"Organic Redox Systems","author":"Lambert C.","year":"2016"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00262H"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60443H"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2012.09.005"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs15339d"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C1CS15165G"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar0000612"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201608973"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201608973"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja101937w"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00075a091"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201604812"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1007\/3-540-29580-1_5"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/cs9952400121"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00081E"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/cc9960001707"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.poly.2014.04.005"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/b418872a"},{"key":"e_1_2_6_23_1","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1002\/9781118858981.ch3","volume-title":"Organic Redox Systems","author":"Kahlfuss C.","year":"2016"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201402805"},{"key":"e_1_2_6_25_1","doi-asserted-by":"crossref","first-page":"383","DOI":"10.1002\/9781118858981.ch12","volume-title":"Organic Redox Systems","author":"Nishinaga T.","year":"2016"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar9600446"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00033a063"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00075a042"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja9533104"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja990777w"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja994259x"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja050783u"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja806207j"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0sc00350f"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201204332"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201502606"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201605842"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b00816"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja964345m"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja065995l"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201200819"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00775a031"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol102339m"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo4015062"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja4081887"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc45125a"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp511608w"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsnano.5b04615"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja001767u"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja000605v"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20010817)7:16<3466::AID-CHEM3466>3.0.CO;2-X"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo401453s"},{"key":"e_1_2_6_53_1","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1002\/9781118858981.ch8","volume-title":"Organic Redox Systems","author":"Suzuki S.","year":"2016"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.131162"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja2035442"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol101997w"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp211391x"},{"key":"e_1_2_6_58_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmr.2005.08.013"},{"key":"e_1_2_6_59_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.67.746"},{"key":"e_1_2_6_60_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp992980j"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(75)80169-2"},{"key":"e_1_2_6_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp057083w"},{"key":"e_1_2_6_63_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.poly.2006.09.034"},{"key":"e_1_2_6_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/ct4010257"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0009-2614(99)00206-7"},{"key":"e_1_2_6_66_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00526a005"},{"key":"e_1_2_6_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0367748"},{"key":"e_1_2_6_68_1","doi-asserted-by":"publisher","DOI":"10.1143\/JPSJ.62.289"},{"key":"e_1_2_6_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b05080"},{"key":"e_1_2_6_70_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja9836242"},{"key":"e_1_2_6_71_1","doi-asserted-by":"publisher","DOI":"10.1021\/cm501438j"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201801712","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201801712","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.201801712","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/am-pdf\/10.1002%2Fchem.201801712","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201801712","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T17:19:12Z","timestamp":1760289552000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201801712"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,7,11]]},"references-count":72,"journal-issue":{"issue":"45","published-print":{"date-parts":[[2018,8,9]]}},"alternative-id":["10.1002\/chem.201801712"],"URL":"https:\/\/doi.org\/10.1002\/chem.201801712","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,7,11]]},"assertion":[{"value":"2018-04-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-07-11","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}