{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,13]],"date-time":"2026-07-13T21:36:57Z","timestamp":1783978617238,"version":"3.55.0"},"reference-count":68,"publisher":"Wiley","issue":"14","license":[{"start":{"date-parts":[[2025,1,22]],"date-time":"2025-01-22T00:00:00Z","timestamp":1737504000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["INST 211\/915-1 FUGG"],"award-info":[{"award-number":["INST 211\/915-1 FUGG"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["INST 20876\/294-1 FUGG"],"award-info":[{"award-number":["INST 20876\/294-1 FUGG"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["431460824, STR1186\/7-1 and STR1186\/7-2"],"award-info":[{"award-number":["431460824, STR1186\/7-1 and STR1186\/7-2"]}],"id":[{"id":"10.13039\/501100001659","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":[[2025,3,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    In recent years, researchers studying fluorogenic samples have steadily shifted from using large, expensive, poorly soluble fluorophores with complex synthetic sequences to smaller, simpler \u03c0 scaffolds with low molecular weight. This research article presents an in\u2010depth study of the photophysical properties of five bridged single\u2010benzene\u2010based fluorophores (SBBFs) investigated for their solution and solid\u2010state emission (SSSE) properties. The compounds\n                    <jats:bold>\n                      O\n                      <jats:sub>4<\/jats:sub>\n                    <\/jats:bold>\n                    ,\n                    <jats:bold>\n                      N\n                      <jats:sub>1<\/jats:sub>\n                      O\n                      <jats:sub>3<\/jats:sub>\n                    <\/jats:bold>\n                    ,\n                    <jats:bold>\n                      N\n                      <jats:sub>2<\/jats:sub>\n                      O\n                      <jats:sub>2<\/jats:sub>\n                    <\/jats:bold>\n                    ,\n                    <jats:bold>\n                      N\n                      <jats:sub>3<\/jats:sub>\n                      O\n                      <jats:sub>1<\/jats:sub>\n                    <\/jats:bold>\n                    , and\n                    <jats:bold>\n                      N\n                      <jats:sub>4<\/jats:sub>\n                    <\/jats:bold>\n                    are derived from a central terephthalonitrile core and vary in the amount of oxygen and nitrogen bridging atoms. These minimalized emitters show full\u2010color tunable emission properties and exhibit moderate\u2010to\u2010high photoluminescence quantum yield values reaching up to 0.78 in dimethyl sulfoxide (DMSO). In addition to demonstrating excellent compatibility in poly(methyl methacrylate) (PMMA) films and additive manufacturing using stereolithography (SLA), white light emission was achieved in both solution and 3D\u2010printed materials by controlling the mixing ratio of the compounds. Employing density\u2010functional theory (DFT), well\u2010correlating theoretical absorption and emission wavelengths were calculated as average values of the different possible conformers. Furthermore, cellular internalization of the substances was accomplished using Pluronic\n                    <jats:sup>\u00ae<\/jats:sup>\n                    F\u2010127 nanoparticles. Overall, this study emphasizes the remarkable properties of single\u2010benzene\u2010based emitters, showcasing their accessibility and potential applications in biomedical fields and materials science.\n                  <\/jats:p>","DOI":"10.1002\/chem.202404263","type":"journal-article","created":{"date-parts":[[2024,12,23]],"date-time":"2024-12-23T11:40:31Z","timestamp":1734954031000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Stepwise Modulation of Bridged Single\u2010Benzene\u2010Based Fluorophores for Materials Science"],"prefix":"10.1002","volume":"31","author":[{"given":"Alexander","family":"Huber","sequence":"first","affiliation":[{"name":"Faculty of Chemistry (Organic Chemistry) CENIDE and Center of Medical Biotechnology (ZMB) University of Duisburg-Essen  Universit\u00e4tsstra\u00dfe 7 45141 Essen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Laura","family":"Schmidt","sequence":"additional","affiliation":[{"name":"Department of Molecular Biology II Center of Medical Biotechnology (ZMB) University of Duisburg-Essen  Universit\u00e4tsstra\u00dfe 2 45141 Essen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tim","family":"Gatz","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry (Organic Chemistry) CENIDE and Center of Medical Biotechnology (ZMB) University of Duisburg-Essen  Universit\u00e4tsstra\u00dfe 7 45141 Essen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jana","family":"Bublitz","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry (Organic Chemistry) CENIDE and Center of Medical Biotechnology (ZMB) University of Duisburg-Essen  Universit\u00e4tsstra\u00dfe 7 45141 Essen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tobias","family":"Rex","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Anorganische und Analytische Chemie CeNTech, CiMIC, SoN Universit\u00e4t M\u00fcnster  Heisenbergstra\u00dfe 11 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sidharth Thulaseedharen Nair","family":"Sailaja","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry (Organic Chemistry) CENIDE and Center of Medical Biotechnology (ZMB) University of Duisburg-Essen  Universit\u00e4tsstra\u00dfe 7 45141 Essen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elisabeth","family":"Verheggen","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry (Organic Chemistry) CENIDE and Center of Medical Biotechnology (ZMB) University of Duisburg-Essen  Universit\u00e4tsstra\u00dfe 7 45141 Essen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lea","family":"H\u00f6fmann","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry (Organic Chemistry) CENIDE and Center of Medical Biotechnology (ZMB) University of Duisburg-Essen  Universit\u00e4tsstra\u00dfe 7 45141 Essen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christoph","family":"W\u00f6lper","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry (Inorganic Chemistry) University of Duisburg-Essen  Universit\u00e4tsstra\u00dfe 7 45141 Essen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cristian A.","family":"Strassert","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Anorganische und Analytische Chemie CeNTech, CiMIC, SoN Universit\u00e4t M\u00fcnster  Heisenbergstra\u00dfe 11 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shirley K.","family":"Knauer","sequence":"additional","affiliation":[{"name":"Department of Molecular Biology II Center of Medical Biotechnology (ZMB) University of Duisburg-Essen  Universit\u00e4tsstra\u00dfe 2 45141 Essen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9612-2306","authenticated-orcid":false,"given":"Jens","family":"Voskuhl","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry (Organic Chemistry) CENIDE and Center of Medical Biotechnology (ZMB) University of Duisburg-Essen  Universit\u00e4tsstra\u00dfe 7 45141 Essen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,1,22]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.3c00605"},{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202204788"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2024.102458"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200900963"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201502365"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201706517"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202011857"},{"key":"e_1_2_9_8_1","author":"Huber A.","year":"2022","journal-title":"Chem. \u2013 Eur. J."},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc35641d"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201501981"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3AN00046J"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.7b12320"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201905169"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcc.6b01351"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB02387F"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC02616H"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201904478"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcc.8b01251"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-021-25677-2"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202403954"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0TC00776E"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202302107"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202301411"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC06260B"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2014.05.031"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/lpor.201600147"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201904626"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.2c00045"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202001999"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3OB01761C"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2024.139340"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202000233"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202100492"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3OB00656E"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202300334"},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemmater.1c02460"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b02523"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.1782"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202200599"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41563-020-0797-2"},{"key":"e_1_2_9_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA27547H"},{"key":"e_1_2_9_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b04404"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules27082443"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.27304"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1098\/rsta.1932.0005"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CS00464J"},{"key":"e_1_2_9_47_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac198860071107"},{"key":"e_1_2_9_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)57338-5"},{"key":"e_1_2_9_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.supmat.2023.100042"},{"key":"e_1_2_9_50_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-019-47847-5"},{"key":"e_1_2_9_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2022.138960"},{"key":"e_1_2_9_52_1","doi-asserted-by":"publisher","DOI":"10.1007\/s42114-022-00483-6"},{"key":"e_1_2_9_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/adom.201900916"},{"key":"e_1_2_9_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/adom.201901912"},{"key":"e_1_2_9_55_1","unstructured":"Deposition Numbers 2393406 (O4) 2393407 (N2O2) 2393405 (N3O1) 2393408 (N4) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures Service."},{"key":"e_1_2_9_56_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576721002910"},{"key":"e_1_2_9_57_1","unstructured":"M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone G.\u2005A. Petersson H. Nakatsuji X. Li M. Caricato A.\u2005V. Marenich J. Bloino B.\u2005G. Janesko R. Gomperts B. Mennucci H.\u2005P. Hratchian J.\u2005V. Ortiz A.\u2005F. Izmaylov J.\u2005L. Sonnenberg D. Williams-Young F. Ding F. Lipparini F. Egidi J. Goings B. Peng A. Petrone T. Henderson D. Ranasinghe V.\u2005G. Zakrzewski J. Gao N. Rega G. Zheng W. Liang M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven K. Throssell J.\u2005A. Montgomery Jr. J.\u2005E. Peralta F. Ogliaro M.\u2005J. Bearpark J.\u2005J. Heyd E.\u2005N. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov T.\u2005A. Keith R. Kobayashi J. Normand K. Raghavachari A.\u2005P. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi J.\u2005M. Millam M. Klene C. Adamo R. Cammi J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma O. Farkas J.\u2005B. Foresman D.\u2005J. Fox Gaussian 16 Revision A.03 2016 Gaussian Inc. Wallingford CT."},{"key":"e_1_2_9_58_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1508368"},{"key":"e_1_2_9_59_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.77.3865"},{"key":"e_1_2_9_60_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.467146"},{"key":"e_1_2_9_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21759"},{"key":"e_1_2_9_62_1","doi-asserted-by":"publisher","DOI":"10.1002\/smll.201503396"},{"key":"e_1_2_9_63_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0pp00381f"},{"key":"e_1_2_9_64_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC05431C"},{"key":"e_1_2_9_65_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767390000277"},{"key":"e_1_2_9_66_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229614024218"},{"key":"e_1_2_9_67_1","unstructured":"Sheldrick G.\u2005M. SHELXL-2017 Program for the Refinement of Crystal Structures University of G\u00f6ttingen G\u00f6ttingen (Germany) 2017."},{"key":"e_1_2_9_68_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889811043202"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202404263","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,11,21]],"date-time":"2025-11-21T15:34:24Z","timestamp":1763739264000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202404263"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,1,22]]},"references-count":68,"journal-issue":{"issue":"14","published-print":{"date-parts":[[2025,3,6]]}},"alternative-id":["10.1002\/chem.202404263"],"URL":"https:\/\/doi.org\/10.1002\/chem.202404263","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,1,22]]},"assertion":[{"value":"2024-11-19","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-01-22","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202404263"}}