{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T20:15:21Z","timestamp":1788984921462,"version":"build-2803163510"},"reference-count":65,"publisher":"Wiley","issue":"20","license":[{"start":{"date-parts":[[2009,3,26]],"date-time":"2009-03-26T00:00:00Z","timestamp":1238025600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2009,5,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:bold>Not common sense, but specific<\/jats:bold>: Dicationic azaborines bearing ammonio or phosphonio groups showed enhanced Lewis acidity as well as improved water solubility. Complexation between the azaborines and fluoride or cyanide ions was observed in aqueous media (see figure; DMSO= dimethyl sulfoxide).<jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/mcontent.gif\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text><\/jats:p><jats:p>New cationic triarylboranes bearing ammonio or phosphonio groups on the periphery were synthesized from a common intermediate, a dibromodibenzoazaborine. These cationic molecules are soluble in highly polar organic solvents as well as water, and they exhibit strong light absorption and photoluminescence emission in water. Complexation of the cationic azaborines with fluoride and cyanide ions in aqueous media proceeded and could be monitored by NMR, UV\/Vis, and fluorescence spectroscopy.<\/jats:p>","DOI":"10.1002\/chem.200802159","type":"journal-article","created":{"date-parts":[[2009,3,26]],"date-time":"2009-03-26T09:10:07Z","timestamp":1238058607000},"page":"5056-5062","source":"Crossref","is-referenced-by-count":106,"title":["Detection of Biologically Important Anions in Aqueous Media by Dicationic Azaborines Bearing Ammonio or Phosphonio Groups"],"prefix":"10.1002","volume":"15","author":[{"given":"Tomohiro","family":"Agou","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masaki","family":"Sekine","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junji","family":"Kobayashi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takayuki","family":"Kawashima","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,5,4]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010202)113:3<502::AID-ANGE502>3.0.CO;2-A"},{"key":"e_1_2_6_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr010421e"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0501339"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/b601511e"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020080k"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar050195l"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-8545(03)00023-7"},{"key":"e_1_2_6_9_2","unstructured":"Environmental Health Criteria No. 227 Fluorides The International Program on Chemical Safety World Health Organization 2002."},{"key":"e_1_2_6_10_2","unstructured":"\u00a0"},{"key":"e_1_2_6_11_2","first-page":"271","volume-title":"Medical Aspects of Chemical and Biological Wafare","author":"Baskin S. 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Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman J.\u2005A. Montgomery \u2005Jr. T. Vreven K.\u2005N. Kudin J.\u2005C. Burant J.\u2005M. Millam S.\u2005S. Iyengar J. Tomasi V. Barone B. Mennucci M. Cossi G. Scalmani N. Rega G.\u2005A. Petersson H. Nakatsuji M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai M. Klene X. Li J.\u2005E. Knox H.\u2005P. Hratchian J.\u2005B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. Austin R. Cammi C. Pomelli J.\u2005W. Ochterski P.\u2005Y. Ayala K. Morokuma G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg V.\u2005G. Zakrzewski S. Dapprich A.\u2005D. Daniels M.\u2005C. Strain O. Farkas D.\u2005K. Malick A.\u2005D. Rabuck K. Raghavachari J.\u2005B. Foresman J.\u2005V. Ortiz Q. Cui A.\u2005G. Baboul S. Clifford J. Cioslowski B.\u2005B. Stefanov G. Liu A. Liashenko P. Piskorz I. Komaromi R.\u2005L. Martin D.\u2005J. Fox T. Keith M.\u2005A. Al\u2010Laham C.\u2005Y. Peng A. Nanayakkara M. Challacombe P.\u2005M.\u2005W. Gill B. Johnson W. Chen M.\u2005W. Wong C. Gonzalez J.\u2005A. Pople Gaussian Inc. Wallingford CT 2004."},{"key":"e_1_2_6_58_2","unstructured":"Weak photoluminescence of1\u2009aand2\u2009ain CH2Cl2may be due to complexation of the iodide ion to the boron centers in the ground or excited state because bis(methyldiphenylphosphonio)azaborine bis(tetraphenylborate)2\u2009dshowed a higher photoluminescence quantum yield (\u03a60.19) in CH2Cl2than that of2\u2009a. In addition the photoluminescence quantum yields of2\u2009ain polar solvents increased more than that in the less polar CH2Cl2(in DMSO:\u03a6=0.57 in MeOH:\u03a6=0.78) indicating that the cation\u2013anion interactions influence the fluorescence property of the dicationic azaborine."},{"key":"e_1_2_6_59_2","first-page":"83","volume-title":"Handbook of Photochemistry","author":"Murov S. L.","year":"1973"},{"key":"e_1_2_6_60_2","unstructured":"In general UV\/Vis absorption of azaborine shows only minor solvent dependency as the degree of intramolecular charge transfer between the nitrogen and boron atoms is not so high. T. Agou J. Kobayashi T. Kawashima unpublished results."},{"key":"e_1_2_6_61_2","unstructured":"Although the complex formation of1\u2009awith the fluoride ion could not be observed by UV\/Vis or fluorescence spectroscopy at higher concentrations ([1\u2009a]=0.04\u2009Min DMSO\/H2O mixture (3:1 v\/v)) the complexation could be monitored by11B and19F\u2005NMR spectroscopy."},{"key":"e_1_2_6_62_2","unstructured":"Although2\u2009adid not react with the fluoride ions in the DMSO\/H2O (4:6) mixture as shown here the complexation could be observed when the amount of DMSO was increased (DMSO\/H2O=3:1 v\/v). See the Supporting Information for details."},{"key":"e_1_2_6_63_2","unstructured":"Complex2\u2009awas treated with solid KF and [18]crown\u20106 or NaCN in CD2Cl2to give2\u2009bor2\u2009cin an almost quantitative yield. Fluoroborate2\u2009bwas characterized by1H 11B and19F\u2005NMR spectroscopy. The formation of cyanoborate2\u2009cwas confirmed by IR spectroscopy (\u03bd(CN)=2163\u2005cm\u22121in a KBr disk) in addition to1H 13C 11B and31P\u2005NMR spectroscopy."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200802159","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200802159","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T16:33:56Z","timestamp":1760286836000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200802159"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,5,4]]},"references-count":65,"journal-issue":{"issue":"20","published-print":{"date-parts":[[2009,5,11]]}},"alternative-id":["10.1002\/chem.200802159"],"URL":"https:\/\/doi.org\/10.1002\/chem.200802159","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,5,4]]}}}