{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,5]],"date-time":"2026-09-05T01:13:53Z","timestamp":1788570833644,"version":"build-2803163510"},"reference-count":92,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2023,11,17]],"date-time":"2023-11-17T00:00:00Z","timestamp":1700179200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001843","name":"Science and Engineering Research Board","doi-asserted-by":"publisher","award":["CRG\/2021\/000017"],"award-info":[{"award-number":["CRG\/2021\/000017"]}],"id":[{"id":"10.13039\/501100001843","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004541","name":"Ministry of Education, India","doi-asserted-by":"publisher","award":["5-5\/2014-TS VII"],"award-info":[{"award-number":["5-5\/2014-TS VII"]}],"id":[{"id":"10.13039\/501100004541","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["aces.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2023,12,14]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:italic>peri<\/jats:italic>\u2010Annulation of naphthalane, an important tool for realization of wide range of functional materials, is presently accomplished with limited few functional groups like imide, amide and diamine\u2010derivative (perimidine). To increase the diversity, we have incorporated \u03b1\u2010keto aldonitrone as a new functional group, and herein report about five <jats:italic>peri<\/jats:italic>\u2010naphthoisatogens (PNTIs) dyes. The synthesis were accomplished using an unusual reaction of aromatic nitro group, which is nucleophilic attack of a C\u2010nucleophile (enol) to the N\u2010atom of nitro group. In five different 5\u2010alkylamino\u20108\u2010nitro\u20101\u2010acetylnaphthalenes, intramolecular acid\u2010catalyzed nucleophilic attack of enol moiety to the N\u2010atom of nitro group produced \u03b1\u2010keto aldonitrone via addition\u2010elimination mechanism. The PNTIs showed characteristics of 1,3\u2010dipole and reacted with ethyl acrylate to produce isoxazolidine ring, which subsequently converted into aza phenalenone derivative via ring cleavage. Both the PNTI and the corresponding derivative strongly absorb in the visible region, displaying absorption maximum at 551 and 561\u2005nm (in CHCl<jats:sub>3<\/jats:sub>) respectively. Compared to the popular analogous dye naphthalene monoimides, PNTIs showed bathochromic shift of absorption maximum by more than 100\u2005nm. The emission maximum for the PNTI and its derivative in chloroform were observed at 594 and 635\u2005nm respectively.<\/jats:p>","DOI":"10.1002\/asia.202300827","type":"journal-article","created":{"date-parts":[[2023,11,6]],"date-time":"2023-11-06T07:23:59Z","timestamp":1699255439000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Stable <i>peri<\/i>\u2010Naphthoisatogens without C2 Protection: Synthesis via Aldrone Condensation, Optical Properties and 1,3\u2010Dipolar Cycloaddition Reaction"],"prefix":"10.1002","volume":"18","author":[{"given":"Indraneel","family":"Debnath","sequence":"first","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology, Guwahati  Guwahati Assam 781039 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tirupati","family":"Roy","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology, Guwahati  Guwahati Assam 781039 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dharismita","family":"Borah","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology, Guwahati  Guwahati Assam 781039 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8453-2650","authenticated-orcid":false,"given":"Kingsuk","family":"Mahata","sequence":"additional","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology, Guwahati  Guwahati Assam 781039 India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,11,17]]},"reference":[{"key":"e_1_2_9_1_1","unstructured":"\u00a0"},{"key":"e_1_2_9_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35467e"},{"key":"e_1_2_9_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.7b14473"},{"key":"e_1_2_9_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0TC03681A"},{"key":"e_1_2_9_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2021.214019"},{"key":"e_1_2_9_6_1","unstructured":"\u00a0"},{"key":"e_1_2_9_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob25798j"},{"key":"e_1_2_9_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309746"},{"key":"e_1_2_9_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00160"},{"key":"e_1_2_9_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201806008"},{"key":"e_1_2_9_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201901390"},{"key":"e_1_2_9_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00239A"},{"key":"e_1_2_9_13_1","unstructured":"\u00a0"},{"key":"e_1_2_9_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b01511"},{"key":"e_1_2_9_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2018.04.048"},{"key":"e_1_2_9_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2TB02528K"},{"key":"e_1_2_9_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2023.111198"},{"key":"e_1_2_9_18_1","unstructured":"\u00a0"},{"key":"e_1_2_9_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b07750"},{"key":"e_1_2_9_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202009359"},{"key":"e_1_2_9_21_1","unstructured":"\u00a0"},{"key":"e_1_2_9_22_2","doi-asserted-by":"publisher","DOI":"10.1007\/s41061-020-00307-5"},{"key":"e_1_2_9_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.1c00189"},{"key":"e_1_2_9_24_1","unstructured":"\u00a0"},{"key":"e_1_2_9_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.18810140238"},{"key":"e_1_2_9_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0065-2725(08)60104-X"},{"key":"e_1_2_9_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19860001005"},{"key":"e_1_2_9_28_1","unstructured":"\u00a0"},{"key":"e_1_2_9_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/bm100814n"},{"key":"e_1_2_9_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201000769"},{"key":"e_1_2_9_31_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2012.60"},{"key":"e_1_2_9_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201501372"},{"key":"e_1_2_9_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC05719F"},{"key":"e_1_2_9_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO00134E"},{"key":"e_1_2_9_35_1","unstructured":"\u00a0"},{"key":"e_1_2_9_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc45512b"},{"key":"e_1_2_9_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201504697"},{"key":"e_1_2_9_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC06418A"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1139\/v71-601"},{"key":"e_1_2_9_40_1","unstructured":"\u00a0"},{"key":"e_1_2_9_41_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5QO00122F"},{"key":"e_1_2_9_42_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC00882J"},{"key":"e_1_2_9_43_1","unstructured":"\u00a0"},{"key":"e_1_2_9_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b02192"},{"key":"e_1_2_9_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB01580F"},{"key":"e_1_2_9_46_1","unstructured":"\u00a0"},{"key":"e_1_2_9_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201904607"},{"key":"e_1_2_9_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c01140"},{"key":"e_1_2_9_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.1c00284"},{"key":"e_1_2_9_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202001558"},{"key":"e_1_2_9_51_1","unstructured":"\u00a0"},{"key":"e_1_2_9_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00543"},{"key":"e_1_2_9_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202001214"},{"key":"e_1_2_9_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB02352F"},{"key":"e_1_2_9_55_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3OB00189J"},{"key":"e_1_2_9_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02178"},{"key":"e_1_2_9_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201400097"},{"key":"e_1_2_9_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr60280a002"},{"key":"e_1_2_9_59_1","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.46-0689"},{"key":"e_1_2_9_60_1","doi-asserted-by":"publisher","DOI":"10.1039\/a607378f"},{"key":"e_1_2_9_61_1","unstructured":"\u00a0"},{"key":"e_1_2_9_62_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19730001310"},{"key":"e_1_2_9_63_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19760000394"},{"key":"e_1_2_9_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo0706729"},{"key":"e_1_2_9_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00271a036"},{"key":"e_1_2_9_66_1","doi-asserted-by":"publisher","DOI":"10.1071\/CH9951969"},{"key":"e_1_2_9_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/om060883o"},{"key":"e_1_2_9_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c00603"},{"key":"e_1_2_9_69_1","unstructured":"Alkylamino group acted as electron donating moiety in acidic medium and directed at para-position during preparation of precursors2-4\u2009r."},{"key":"e_1_2_9_70_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02495619"},{"key":"e_1_2_9_71_1","unstructured":"\u00a0"},{"key":"e_1_2_9_72_2","doi-asserted-by":"publisher","DOI":"10.1135\/cccc2008216"},{"key":"e_1_2_9_73_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39730000096"},{"key":"e_1_2_9_74_2","doi-asserted-by":"publisher","DOI":"10.3390\/70100007"},{"key":"e_1_2_9_75_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201702204"},{"key":"e_1_2_9_76_1","unstructured":"\u00a0"},{"key":"e_1_2_9_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00476"},{"key":"e_1_2_9_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201900718"},{"key":"e_1_2_9_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00832"},{"key":"e_1_2_9_80_1","unstructured":"\u00a0"},{"key":"e_1_2_9_81_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201702330"},{"key":"e_1_2_9_82_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1NJ02023D"},{"key":"e_1_2_9_83_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CP01016H"},{"key":"e_1_2_9_84_1","unstructured":"\u00a0"},{"key":"e_1_2_9_85_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201705546"},{"key":"e_1_2_9_86_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201905248"},{"key":"e_1_2_9_87_1","volume":"114","author":"Lee C.-W.","year":"2010","journal-title":"J. Phys. Chem. C"},{"key":"e_1_2_9_88_1","doi-asserted-by":"crossref","unstructured":"C. Reichardt T. Welton Solvents and solvent effects in organic chemistry Wiley-VCH Weinheim Germany 2011(4th updated and enl. ed edn.).","DOI":"10.1002\/9783527632220"},{"key":"e_1_2_9_89_1","doi-asserted-by":"publisher","DOI":"10.1039\/c8pp00302e"},{"key":"e_1_2_9_90_1","unstructured":"\u00a0"},{"key":"e_1_2_9_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201808256"},{"key":"e_1_2_9_92_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00948B"}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.202300827","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T11:23:57Z","timestamp":1759922637000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.202300827"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,11,17]]},"references-count":92,"journal-issue":{"issue":"24","published-print":{"date-parts":[[2023,12,14]]}},"alternative-id":["10.1002\/asia.202300827"],"URL":"https:\/\/doi.org\/10.1002\/asia.202300827","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"value":"1861-4728","type":"print"},{"value":"1861-471X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,11,17]]},"assertion":[{"value":"2023-09-21","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-11-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202300827"}}