{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,16]],"date-time":"2026-07-16T20:56:38Z","timestamp":1784235398632,"version":"3.55.0"},"reference-count":45,"publisher":"Wiley","issue":"65","license":[{"start":{"date-parts":[[2022,9,19]],"date-time":"2022-09-19T00:00:00Z","timestamp":1663545600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["91956126"],"award-info":[{"award-number":["91956126"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22171160"],"award-info":[{"award-number":["22171160"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001711","name":"Schweizerischer Nationalfonds zur F\u00f6rderung der Wissenschaftlichen Forschung","doi-asserted-by":"publisher","award":["200020-169077"],"award-info":[{"award-number":["200020-169077"]}],"id":[{"id":"10.13039\/501100001711","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2022,11,21]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The small Stokes shift and weak emission in the solid state are two main shortcomings associated with the boron\u2010dipyrromethene (BODIPY) family of dyes. This study presents the design, synthesis and luminescent properties of boron difluoro complexes of 2\u2010aryl\u20105\u2010alkylamino\u20104\u2010alkylaminocarbonylthiazoles. These dyes display Stokes shifts (\u0394\u03bb, 77\u2013101\u2005nm) with quantum yields (<jats:italic>\u03d5<\/jats:italic><jats:sub>FL<\/jats:sub>) up to 64.9 and 34.7\u2009% in toluene solution and in solid state, respectively. Some of these compounds exhibit dual fluorescence and room\u2010temperature phosphorescence (RTP) emission properties with modulable phosphorescence quantum yields (<jats:italic>\u03d5<\/jats:italic><jats:sub>PL<\/jats:sub>) and lifetime (\u03c4<jats:sub>p<\/jats:sub> up to 251\u2005\u03bcs). The presence of intramolecular H\u2010bonds and negligible \u03c0\u2010\u03c0 stacking revealed by X\u2010ray crystal structure might account for the observed large Stokes shift and significant solid\u2010state emission of these fluorophores, while the enhanced spin\u2010orbit coupling (SOC) of iodine and the self\u2010assembly driven by halogen bonding, \u03c0\u2010\u03c0 and C\u2212H<jats:sup>\u2026<\/jats:sup>\u03c0 interactions could be responsible for the observed RTP of iodine containing phosphors.<\/jats:p>","DOI":"10.1002\/chem.202202507","type":"journal-article","created":{"date-parts":[[2022,8,22]],"date-time":"2022-08-22T12:34:26Z","timestamp":1661171666000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Thiazole Boron Difluoride Dyes with Large Stokes Shift, Solid State Emission and Room\u2010Temperature Phosphorescence"],"prefix":"10.1002","volume":"28","author":[{"given":"Wei","family":"Wang","sequence":"first","affiliation":[{"name":"Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry Chinese Academy of Sciences  Beijing 100190 P. 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China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8390-6689","authenticated-orcid":false,"given":"Jieping","family":"Zhu","sequence":"additional","affiliation":[{"name":"Laboratory of Synthesis and Natural Products (LSPN) Institute of Chemical Sciences and Engineering Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, EPFL-SB-ISIC-LSPN, BCH5304  1015 Lausanne Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,9,19]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr078381n"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201305554"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201305554"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00030K"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00234H"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60411J"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26010153"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C1CS15132K"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00030G"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201105228"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201105228"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200600841"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB00623J"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3CC48316A"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b01363"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00782"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8QM00184G"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol302347m"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201500033"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol400849a"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304824"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304824"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo402583y"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/C1SC00658D"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol400605x"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202004444"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6DT03469A"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC06704E"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol503379c"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201701526"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201603837"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6DT01226D"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201900383"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja2005175"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00364D"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b00859"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201915433"},{"key":"e_1_2_8_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201915433"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC05502A"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b12800"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC04901J"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201702488"},{"key":"e_1_2_8_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201702488"},{"key":"e_1_2_8_39_1","unstructured":"Six-membered borates using secondary amide as an anionic O donor is known see Ref.\u2005[16]."},{"key":"e_1_2_8_40_1","unstructured":"Deposition Numbers993648 (for2\u2009a) 2173871 (for2\u2009b) 2173872 (for2\u2009e) 2173873 (for2\u2009h) 2173874 (for2\u2009k) 2173875 (for2\u2009o) 2173876 (for2\u2009q) 2173877 (for2\u2009s) 2173878 (for2\u2009t) 2173879 (for2\u2009u)contain the supplementary crystallographic data for this paper. 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