{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,28]],"date-time":"2026-08-28T00:44:10Z","timestamp":1787877850241,"version":"build-2784847793"},"reference-count":75,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2013,10,21]],"date-time":"2013-10-21T00:00:00Z","timestamp":1382313600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2014,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A search for novel organic luminogens led us to design and synthesize some N\u2010fused imidazole derivatives based on imidazo[1,2\u2010<jats:italic>a<\/jats:italic>]pyridine as the core and arylamine and imidazole as the peripheral groups. The fluorophores were synthesized through a multicomponent cascade reaction (A<jats:sup>3<\/jats:sup> coupling) of a heterocyclic azine with an aldehyde and alkyne, followed by Suzuki coupling and a multicomponent cyclization reaction. All of the compounds exhibited interesting photophysical responses, especially arylamine\u2010containing derivatives, which displayed strong positive solvatochromism in the emission spectra that indicated a more polar excited state owing to an efficient charge migration from the donor arylamine to the imidazo[1,2\u2010<jats:italic>a<\/jats:italic>]pyridine acceptor. The quantum yields ranged from 0.2 to 0.7 and depended on the substitution pattern, most notably that based on the donor group at the C2 position. Moreover, the influence of general and specific solvent effects on the photophysical properties of the fluorophores was discussed with four\u2010parameter Catal\u00e1n and Kamlet\u2013Taft solvent scales. The excellent thermal, electrochemical, and morphological stability of the compounds was explored by cyclic voltammetry, thermogravimetric analysis, and AFM methods. Furthermore, to understand the structure, bonding, and band gap of the molecules, DFT calculations were performed. The performance of the electroluminescence behavior of the imidazo[1,2\u2010<jats:italic>a<\/jats:italic>]pyridine derivative was investigated by fabricating a multilayer organic light\u2010emitting diode with a configuration of ITO\/NPB (60\u2005nm)\/EML (40\u2005nm)\/BCP (15\u2005nm)\/Alq<jats:sub>3<\/jats:sub> (20\u2005nm)\/LiF (0.5\u2005nm)\/Al(100\u2005nm) (ITO=indium tin oxide, EML=emissive layer, BCP=2,9\u2010dimethyl\u20104,7\u2010diphenyl\u20101,10\u2010phenanthroline, Alq<jats:sub>3<\/jats:sub>=tris(8\u2010hydroxyquinolinato)aluminum), which exhibited white emission with a turn\u2010on voltage of 8\u2005V and a brightness of 22\u2005cd\u2009m<jats:sup>\u22122<\/jats:sup>.<\/jats:p>","DOI":"10.1002\/asia.201301061","type":"journal-article","created":{"date-parts":[[2013,10,21]],"date-time":"2013-10-21T16:12:10Z","timestamp":1382371930000},"page":"294-304","source":"Crossref","is-referenced-by-count":61,"title":["Highly Emissive Luminogens Based on Imidazo[1,2\u2010<i>a<\/i>]pyridine for Electroluminescent Applications"],"prefix":"10.1002","volume":"9","author":[{"given":"Natarajan","family":"Nagarajan","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gunasekaran","family":"Velmurugan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Asit","family":"Prakash","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nanda","family":"Shakti","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Monica","family":"Katiyar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ponnambalam","family":"Venuvanalingam","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rajalingam","family":"Renganathan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,10,21]]},"reference":[{"key":"e_1_2_7_1_2","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200903492"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.201101153"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201200281"},{"key":"e_1_2_7_5_2","unstructured":"\u00a0"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/a701030c"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0ob01179g"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200530g"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic102499h"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300249"},{"key":"e_1_2_7_11_2","unstructured":"\u00a0"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.98799"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-0-387-21720-8"},{"key":"e_1_2_7_14_2","unstructured":"\u00a0"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200305619"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr000013v"},{"key":"e_1_2_7_17_2","unstructured":"\u00a0"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/b315301k"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.200900561"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp311360p"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc00803f"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja806703v"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm300416y"},{"key":"e_1_2_7_24_2","unstructured":"\u00a0"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/aenm.201100026"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CP42993D"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp310425z"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc12163d"},{"key":"e_1_2_7_29_2","unstructured":"\u00a0"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm7022136"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200805257"},{"key":"e_1_2_7_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200805257"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc39243k"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-008044992-0.01010-5"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1sc00122a"},{"key":"e_1_2_7_35_2","unstructured":"\u00a0"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-3565(24)29292-2"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1097\/00004850-198604000-00006"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.2165\/00023210-200519010-00008"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1097\/00008877-199503000-00003"},{"key":"e_1_2_7_40_2","unstructured":"\u00a0"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.01293-09"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301858j"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.72.1327"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100001a014"},{"key":"e_1_2_7_45_2","unstructured":"\u00a0"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200803975"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/am200022z"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201300058"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.462103"},{"key":"e_1_2_7_50_2","unstructured":"\u00a0"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp075653h"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200900244"},{"key":"e_1_2_7_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2006874"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1jm10321k"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm201789u"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2012.05.007"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100550a010"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00165a018"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp8095727"},{"key":"e_1_2_7_60_2","unstructured":"Gaussian\u200509 Revision\u2005D.01 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone B. Mennucci G.\u2005A. Petersson H. Nakatsuji M. Caricato X. Li H.\u2005P. Hratchian A.\u2005F. Izmaylov J. Bloino G. Zheng J.\u2005L. Sonnenberg M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven J.\u2005A. Montgomery J.\u2005E. Peralta F. Ogliaro M. Bearpark J.\u2005J. Heyd E. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov R. Kobayashi J. Normand K. Raghavachari A. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi N. Rega J.\u2005M. Millam M. Klene J.\u2005E. Knox 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 R.\u2005L. Martin K. Morokuma V.\u2005G. Zakrzewski G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg S. Dapprich A.\u2005D. Daniels Farkas J.\u2005B. Foresman J.\u2005V. Ortiz J. Cioslowski D.\u2005J. Fox Wallingford CT 2009."},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo3003024"},{"key":"e_1_2_7_62_2","unstructured":"\u00a0"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochem.2010.12.018"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11172-008-0145-1"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2tc00474g"},{"key":"e_1_2_7_66_2","volume-title":"Principles of Fluorescence Spectroscopy","author":"Lakowicz J. R.","year":"2007"},{"key":"e_1_2_7_67_2","unstructured":"\u00a0"},{"key":"e_1_2_7_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo302309m"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ta01657a"},{"key":"e_1_2_7_70_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.363140"},{"key":"e_1_2_7_71_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc14534g"},{"key":"e_1_2_7_72_2","unstructured":"A.\u2005L. Tenderholt Ph.D. Thesis Stanford University Stanford CA USA 2007."},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp8028215"},{"key":"e_1_2_7_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm9017503"}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fasia.201301061","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.201301061","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T19:48:20Z","timestamp":1759952900000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.201301061"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,10,21]]},"references-count":75,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2014,1]]}},"alternative-id":["10.1002\/asia.201301061"],"URL":"https:\/\/doi.org\/10.1002\/asia.201301061","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"value":"1861-4728","type":"print"},{"value":"1861-471X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,10,21]]}}}