{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T09:16:12Z","timestamp":1789722972798,"version":"4.0.1"},"reference-count":41,"publisher":"Wiley","issue":"41","license":[{"start":{"date-parts":[[2016,8,19]],"date-time":"2016-08-19T00:00:00Z","timestamp":1471564800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004663","name":"Ministry of Science and Technology, Taiwan","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100004663","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2016,10,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A series of compounds containing 5\u2010(2\u2010aminobenzylidene)\u20102,3\u2010dimethyl\u20103,5\u2010dihydro\u20104<jats:italic>H<\/jats:italic>\u2010imidazol\u20104\u2010one (<jats:italic><jats:bold>o<\/jats:bold><\/jats:italic><jats:bold>\u2010ABDI<\/jats:bold>) as the core chromophore with a seven\u2010membered\u2010ring N\u2212H\u2010type intramolecular hydrogen bond have been synthesized and characterized. The acidity of the N\u2212H proton and thus the hydrogen\u2010bond strength can be fine\u2010tuned by replacing one of the amino hydrogen atoms by a substituent R, the acidity increasing with increasing electron\u2010withdrawing strength of R, that is, in the order H&lt;COCH<jats:sub>3<\/jats:sub>&lt;COPh&lt;Tosyl&lt;COCF<jats:sub>3<\/jats:sub>. The tosyl and trifluoroacetyl derivatives undergo ultrafast, irreversible excited\u2010state intramolecular proton transfer (ESIPT) that results in proton\u2010transfer emission solely in the red region. Reversible ESIPT, and hence dual emission, involving the normal and proton\u2010transfer tautomers was resolved for the acetyl\u2010 and benzyl\u2010substituted counterparts. For <jats:italic><jats:bold>o<\/jats:bold><\/jats:italic><jats:bold>\u2010ABDI<\/jats:bold>, which has the weakest acidity, ESIPT is prohibited due to its highly endergonic reaction. The results clearly demonstrate the harnessing of ESIPT by modifying the proton acidity and hydrogen\u2010bonding strength in a seven\u2010membered\u2010ring intramolecular hydrogen\u2010bonding system. For all the compounds studied, the emission quantum yields are weak (ca. 10<jats:sup>\u22123<\/jats:sup>) in dichloromethane, but strong in the solid form, ranging from 3.2 to 47.4\u2009%.<\/jats:p>","DOI":"10.1002\/chem.201602425","type":"journal-article","created":{"date-parts":[[2016,8,19]],"date-time":"2016-08-19T04:23:08Z","timestamp":1471580588000},"page":"14688-14695","source":"Crossref","is-referenced-by-count":42,"title":["N\u2212H\u2010Type Excited\u2010State Proton Transfer in Compounds Possessing a Seven\u2010Membered\u2010Ring Intramolecular Hydrogen Bond"],"prefix":"10.1002","volume":"22","author":[{"given":"Yi\u2010An","family":"Chen","sequence":"first","affiliation":[{"name":"Department of Chemistry Center for Emerging Material and Advanced Devices National Taiwan University  Taipei 10617 Taiwan R.O.C."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1745-1636","authenticated-orcid":false,"given":"Fan\u2010Yi","family":"Meng","sequence":"additional","affiliation":[{"name":"Department of Chemistry Center for Emerging Material and Advanced Devices National Taiwan University  Taipei 10617 Taiwan R.O.C."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yen\u2010Hao","family":"Hsu","sequence":"additional","affiliation":[{"name":"Department of Chemistry Center for Emerging Material and Advanced Devices National Taiwan University  Taipei 10617 Taiwan R.O.C."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cheng\u2010Hsien","family":"Hung","sequence":"additional","affiliation":[{"name":"Department of Chemistry Center for Emerging Material and Advanced Devices National Taiwan University  Taipei 10617 Taiwan R.O.C."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chi\u2010Lin","family":"Chen","sequence":"additional","affiliation":[{"name":"Department of Chemistry Center for Emerging Material and Advanced Devices National Taiwan University  Taipei 10617 Taiwan R.O.C."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kun\u2010You","family":"Chung","sequence":"additional","affiliation":[{"name":"Department of Chemistry Center for Emerging Material and Advanced Devices National Taiwan University  Taipei 10617 Taiwan R.O.C."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei\u2010Feng","family":"Tang","sequence":"additional","affiliation":[{"name":"Institute of Optoelectronic Sciences National Taiwan Ocean University  Keelung 20224 Taiwan R.O.C."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wen\u2010Yi","family":"Hung","sequence":"additional","affiliation":[{"name":"Institute of Optoelectronic Sciences National Taiwan Ocean University  Keelung 20224 Taiwan R.O.C."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pi\u2010Tai","family":"Chou","sequence":"additional","affiliation":[{"name":"Department of Chemistry Center for Emerging Material and Advanced Devices National Taiwan University  Taipei 10617 Taiwan R.O.C."}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,8,19]]},"reference":[{"key":"e_1_2_6_1_1","first-page":"1144","volume":"60","author":"Weller A.","year":"1956","journal-title":"Z. 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