{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T06:21:48Z","timestamp":1790662908754,"version":"4.1.0"},"reference-count":68,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2014,12,23]],"date-time":"2014-12-23T00:00:00Z","timestamp":1419292800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE1213574"],"award-info":[{"award-number":["CHE1213574"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Photochem &amp; Photobiology"],"published-print":{"date-parts":[[2015,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>2\u2010(2\u2032\u2010Hydroxyphenyl)benzoxazole (<jats:styled-content style=\"fixed-case\">HBO<\/jats:styled-content>) is known for undergoing intramolecular proton transfer in the excited state to result in the emission of its tautomer. A minor long\u2010wavelength absorption band in the range 370\u2013420\u00a0nm has been reported in highly polar solvents such as dimethylsulfoxide (<jats:styled-content style=\"fixed-case\">DMSO<\/jats:styled-content>). However, the nature of this species has not been entirely clarified. In this work, we provide evidence that this long\u2010wavelength absorption band might have been caused by base or metal salt impurities that are introduced into the spectral sample during solvent transport using glass Pasteur pipettes. The contamination by base or metal salt could be avoided by using borosilicate glass syringes or nonglass pipettes in sample handling. Quantum chemical calculations conclude that solvent\u2010mediated deprotonation is too energetically costly to occur without the aid of a base of an adequate strength. In the presence of such a base, the deprotonation of <jats:styled-content style=\"fixed-case\">HBO<\/jats:styled-content> and its effect on emission are investigated in dichloromethane and <jats:styled-content style=\"fixed-case\">DMSO<\/jats:styled-content>, the latter of which facilitates deprotonation much more readily than the former. Finally, the absorption and emission spectra of <jats:styled-content style=\"fixed-case\">HBO<\/jats:styled-content> in 13 solvents are reported, from which it is concluded that <jats:styled-content style=\"fixed-case\">ESIPT<\/jats:styled-content> is hindered in polar solvents that are also strong hydrogen bond acceptors.<\/jats:p>","DOI":"10.1111\/php.12393","type":"journal-article","created":{"date-parts":[[2014,11,18]],"date-time":"2014-11-18T09:57:10Z","timestamp":1416304630000},"page":"586-598","source":"Crossref","is-referenced-by-count":29,"title":["Absorption and Emission Sensitivity of 2\u2010(2\u2032\u2010Hydroxyphenyl)benzoxazole to Solvents and Impurities"],"prefix":"10.1111","volume":"91","author":[{"given":"Zhao","family":"Yuan","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry Florida State University Tallahassee FL"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qing","family":"Tang","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California Riverside CA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kesavapillai","family":"Sreenath","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Florida State University Tallahassee FL"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J. Tyler","family":"Simmons","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Florida State University Tallahassee FL"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ali H.","family":"Younes","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Florida State University Tallahassee FL"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"De\u2010en","family":"Jiang","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California Riverside CA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lei","family":"Zhu","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Florida State University Tallahassee FL"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,12,23]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/j29670000317"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/j29670000321"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(82)83624-5"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/0301-0104(83)85078-2"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00292a018"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/0047-2670(86)87011-3"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(87)80459-1"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp013915o"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1070\/RC1977v046n01ABEH002116"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.pc.37.100186.001015"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar990109f"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp311709c"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/f29868202379"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/1010-6030(93)80158-6"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.80.6.1767"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/j150664a032"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1751-1097.1998.tb09677.x"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp810256x"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1111\/php.12257"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100720a003"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac197336010141"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp961382r"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1070\/RC2011v080n06ABEH004144"},{"key":"e_1_2_6_25_1","unstructured":"The ground and excited state conformational analysis of HBO in both vacuum and\/or solvent (ethanol) was described in references 25\u201327. Two conformers that contain N\u00b7\u00b7\u00b7H\u2010O and O\u00b7\u00b7\u00b7H\u2010O hydrogen bonds respectively are relatively stable. The O\u00b7\u00b7\u00b7H\u2010O bonded conformer might twist out of planarity according to references 26 and 27."},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100146a008"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100088a006"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/a908359f"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/cm702527m"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.3116\/16091833\/14\/1\/1\/2013"},{"key":"e_1_2_6_31_1","unstructured":"For convenience only the planar conformations are drawn in this work with the understanding that the distribution of conformers is dependent on solvent and protonation state."},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00353a047"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/j150655a012"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(90)85274-G"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp014634j"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp971566l"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp074726u"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1934603100"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja039073j"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200305299"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol200054w"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc39256b"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3tb21339k"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201300816"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/c4sc00308j"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00280F"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp900688h"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja902533f"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja2062693"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(19)83641-4"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10895-010-0644-y"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200902148"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201102046"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja047815i"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201402717"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(89)85118-8"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1039\/P29930000799"},{"key":"e_1_2_6_58_1","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35195A"},{"key":"e_1_2_6_59_1","first-page":"1055","volume":"27","author":"Stryukov M. B.","year":"1977","journal-title":"Zh. Prikl. Spektroskopii"},{"key":"e_1_2_6_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemphys.2007.06.023"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600536805027066"},{"key":"e_1_2_6_62_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF01876657"},{"key":"e_1_2_6_63_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar00156a004"},{"key":"e_1_2_6_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100086a014"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1104038"},{"key":"e_1_2_6_66_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100297a011"},{"key":"e_1_2_6_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100297a012"},{"key":"e_1_2_6_68_1","unstructured":"Very slightly blue shifted absorption spectra in hydrogen bond\u2010donating solvents were noted in references 8 and 60."},{"key":"e_1_2_6_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00165a018"}],"container-title":["Photochemistry and Photobiology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1111%2Fphp.12393","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/php.12393","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,16]],"date-time":"2023-09-16T05:09:38Z","timestamp":1694840978000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1111\/php.12393"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,12,23]]},"references-count":68,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2015,5]]}},"alternative-id":["10.1111\/php.12393"],"URL":"https:\/\/doi.org\/10.1111\/php.12393","archive":["Portico"],"relation":{},"ISSN":["0031-8655","1751-1097"],"issn-type":[{"value":"0031-8655","type":"print"},{"value":"1751-1097","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,12,23]]}}}