{"created":"2023-05-15T12:35:37.731600+00:00","id":4613,"links":{},"metadata":{"_buckets":{"deposit":"8b583804-c0bc-444a-86c3-abb9ebfbec77"},"_deposit":{"created_by":3,"id":"4613","owners":[3],"pid":{"revision_id":0,"type":"depid","value":"4613"},"status":"published"},"_oai":{"id":"oai:nitech.repo.nii.ac.jp:00004613","sets":["31"]},"author_link":["14519","14522","14518","14520","14527","14524","14526","14525","10534","8643","10536"],"item_10001_biblio_info_28":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"1999-01-01","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"5","bibliographicPageEnd":"995","bibliographicPageStart":"985","bibliographicVolumeNumber":"1999","bibliographic_titles":[{"bibliographic_title":"Journal of the Chemical Society. Perkin transactions 2"}]}]},"item_10001_description_36":{"attribute_name":"内容記述","attribute_value_mlt":[{"subitem_description":"Mesoionic 5,5′-azinobis(1,3-diphenyltetrazole) 1 was prepared, and its chemical oxidation gave stable crystals of the corresponding radical cation 1?+ and dication 12+, which reversibly gave back azine 1 on reduction with zinc. Electrochemical investigations of 1 using cyclovoltammetry and differential pulse voltammetry in pyridine (Py) or dichloromethane (DCM) also revealed the two reversible successive one-electron oxidations leading to dication 12+via radical cation 1?+, both of which can be reduced to the neutral state 1. In the cathodic process, 1 was reduced by two consecutive one-electron transfers at only slightly different potentials up to the corresponding dianion 12? which could be re-oxidized to the neutral state; thus constituting a reversible four-stage redox system. Radical cation 1?+ and anion 1?- were characterized by EPR spectroscopy. In order to get more insights into the spin-density distribution of 1?+, the bis- and tetra-15N-labelled species 1a?+, 1b?+ and 1c?+ were synthesized and investigated by EPR and 15N as well as 14N ENDOR spectroscopy, revealing that the largest N hyperfine coupling constants are due to the nitrogen atoms of the central bridge. According to 1H ENDOR there seems to be a small coupling with the protons of both phenyl rings which cannot be resolved in the EPR spectrum.The electrochemical properties of the related mesoionic compounds 5-10 were also investigated in Py or DCM solutions. In the cathodic process, a reduction peak of 9 and 10 was observed due to their reversible one-electron reduction to the corresponding radical anions. The radical obtained on reduction of 10 was characterized by EPR spectroscopy. On the other hand, 5-8 can be reduced by a formal two-electron transfer up to the corresponding dianions which are re-oxidizable to the neutral state. In the anodic process, 9/10 undergo irreversible one-electron oxidations whereas 5/6 (in DCM) and 7/8 (in Py) experience reversible or irreversible step by step two-electron oxidations leading to the dications. In Py the oxidation products of 5/6 react to further species revealing two more oxidation and several rereduction peaks. On the other hand, the oxidation products of 7/8 are instable in DCM (one main oxidation and rereduction peak). The electrochemical data are discussed in terms of delocalization in the cations and conjugation in the dications.","subitem_description_type":"Other"}]},"item_10001_description_38":{"attribute_name":"フォーマット","attribute_value_mlt":[{"subitem_description":"application/pdf","subitem_description_type":"Other"}]},"item_10001_full_name_27":{"attribute_name":"著者別名","attribute_value_mlt":[{"nameIdentifiers":[{}],"names":[{"name":"荒木, 修喜"}]},{"nameIdentifiers":[{},{}],"names":[{"name":"山村, 初雄"}]}]},"item_10001_publisher_29":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"Royal Society of Chemistry"}]},"item_10001_relation_34":{"attribute_name":"DOI","attribute_value_mlt":[{"subitem_relation_name":[{"subitem_relation_name_text":"10.1039/A809386E"}],"subitem_relation_type":"isIdenticalTo","subitem_relation_type_id":{"subitem_relation_type_id_text":"http://dx.doi.org/10.1039/A809386E","subitem_relation_type_select":"DOI"}}]},"item_10001_source_id_30":{"attribute_name":"ISSN","attribute_value_mlt":[{"subitem_source_identifier":"03009580","subitem_source_identifier_type":"ISSN"}]},"item_10001_source_id_32":{"attribute_name":"書誌レコードID（NCID）","attribute_value_mlt":[{"subitem_source_identifier":"AA00695145","subitem_source_identifier_type":"NCID"}]},"item_10001_version_type_33":{"attribute_name":"著者版フラグ","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_970fb48d4fbd8a85","subitem_version_type":"VoR"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Araki, Shuki","creatorNameLang":"en"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Yamamoto, Kaori","creatorNameLang":"en"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Inoue, Tomoko","creatorNameLang":"en"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Fujimoto, Koji","creatorNameLang":"en"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Yamamura, Hatsuo","creatorNameLang":"en"}],"nameIdentifiers":[{},{}]},{"creatorNames":[{"creatorName":"Kawai, Masao","creatorNameLang":"en"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Butsugan, Yasuo","creatorNameLang":"en"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Zhou, Jinkui","creatorNameLang":"en"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Eichhorn, Emerich","creatorNameLang":"en"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Rieker, Anton","creatorNameLang":"en"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Huber, Martina","creatorNameLang":"en"}],"nameIdentifiers":[{}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2017-01-23"}],"displaytype":"detail","filename":"JCSP 1999_985.pdf","filesize":[{"value":"374.2 kB"}],"format":"application/pdf","license_note":"J. Chem. Soc., Perkin Trans. 2, 1999, 985-995 -Reproduced by permission of The Royal Society of Chemistry (RSC)","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"本文_fulltext","url":"https://nitech.repo.nii.ac.jp/record/4613/files/JCSP 1999_985.pdf"},"version_id":"a60ecf7b-846a-4c0d-b82a-ff9f52a05e22"}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"journal article","resourceuri":"http://purl.org/coar/resource_type/c_6501"}]},"item_title":"Synthesis, electrochemical investigation and EPR spectroscopy of a reversible four-stage redox system based on mesoionic 5,5'-azinobis(1,3-diphenyltetrazole) and related mesoionic compounds","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Synthesis, electrochemical investigation and EPR spectroscopy of a reversible four-stage redox system based on mesoionic 5,5'-azinobis(1,3-diphenyltetrazole) and related mesoionic compounds","subitem_title_language":"en"}]},"item_type_id":"10001","owner":"3","path":["31"],"pubdate":{"attribute_name":"公開日","attribute_value":"2012-11-06"},"publish_date":"2012-11-06","publish_status":"0","recid":"4613","relation_version_is_last":true,"title":["Synthesis, electrochemical investigation and EPR spectroscopy of a reversible four-stage redox system based on mesoionic 5,5'-azinobis(1,3-diphenyltetrazole) and related mesoionic compounds"],"weko_creator_id":"3","weko_shared_id":3},"updated":"2023-05-16T14:15:41.912411+00:00"}