{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,12]],"date-time":"2026-07-12T07:07:58Z","timestamp":1783840078423,"version":"3.55.0"},"reference-count":59,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2026,5,18]],"date-time":"2026-05-18T00:00:00Z","timestamp":1779062400000},"content-version":"vor","delay-in-days":17,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,5,1]],"date-time":"2026-05-01T00:00:00Z","timestamp":1777593600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["aces.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2026,5]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Near\u2010infrared (NIR) fluorescent dyes are promising materials for bio\u2010imaging and security applications. However, achieving efficient photoluminescence (PL) over 1000\u00a0nm is still challenging due to the energy gap law. Herein, we report new intramolecular charge transfer\u2010type fluorescent dyes\n                    <jats:bold>1\u2010H<\/jats:bold>\n                    and\n                    <jats:bold>\n                      1\u2010\n                      <jats:italic>t<\/jats:italic>\n                      \u2010Bu\n                    <\/jats:bold>\n                    bearing pyrazino[2,3\u2010\n                    <jats:italic>b<\/jats:italic>\n                    ]quinoxaline\u20102,3\u2010dicarbonitrile as an electron acceptor unit. In toluene, these dyes exhibited NIR emission at 947 and 979\u00a0nm, with PL quantum yields of 1.04% and 0.12%, respectively. Remarkably, crystallization led to substantial red shifts of their PL spectra to 1076 and 1268\u00a0nm, respectively. X\u2010ray crystallographic analysis revealed the formation of dimeric species involving intermolecular \u03c0\u2013\u03c0 stacking between the donor and acceptor units for\n                    <jats:bold>1\u2010H<\/jats:bold>\n                    and between the acceptor units for\n                    <jats:bold>\n                      1\u2010\n                      <jats:italic>t<\/jats:italic>\n                      \u2010Bu\n                    <\/jats:bold>\n                    . Furthermore, TD\u2010DFT calculations indicated that the red shifts of PL are caused by the intermolecular charge transfer interaction. These combined experimental and theoretical results highlighted the crucial roles of molecular packing in tuning solid\u2010state photophysical properties of ICT dyes exhibiting PL over 1000\u00a0nm.\n                  <\/jats:p>","DOI":"10.1002\/asia.70787","type":"journal-article","created":{"date-parts":[[2026,5,18]],"date-time":"2026-05-18T14:20:32Z","timestamp":1779114032000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Development of Intramolecular Charge Transfer\u2010Type NIR Fluorescent Dyes Bearing a Pyrazino[2,3\u2010\n                    <i>b<\/i>\n                    ]quinoxaline\u2010Based Electron Acceptor"],"prefix":"10.1002","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-9703-1222","authenticated-orcid":false,"given":"Masaki","family":"Nagaoka","sequence":"first","affiliation":[{"name":"Graduate School of Engineering Osaka Metropolitan University Sakai\u2010shi Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6187-8664","authenticated-orcid":false,"given":"Naoya","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Graduate School of Engineering Osaka Metropolitan University Sakai\u2010shi Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4190-9539","authenticated-orcid":false,"given":"Shintaro","family":"Kodama","sequence":"additional","affiliation":[{"name":"Graduate School of Engineering Osaka Metropolitan University Sakai\u2010shi Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4382-6788","authenticated-orcid":false,"given":"Takeshi","family":"Maeda","sequence":"additional","affiliation":[{"name":"Graduate School of Engineering Osaka Metropolitan University Sakai\u2010shi Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6503-1607","authenticated-orcid":false,"given":"Daisuke","family":"Sakamaki","sequence":"additional","affiliation":[{"name":"Graduate School of Science Osaka Metropolitan University Osaka\u2010shi Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4287-1547","authenticated-orcid":false,"given":"Hideki","family":"Fujiwara","sequence":"additional","affiliation":[{"name":"Graduate School of Science Osaka Metropolitan University Osaka\u2010shi Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takuya","family":"Omine","sequence":"additional","affiliation":[{"name":"Graduate School of Engineering The University of Osaka Suita\u2010shi Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7429-2200","authenticated-orcid":false,"given":"Akinori","family":"Saeki","sequence":"additional","affiliation":[{"name":"Graduate School of Engineering The University of Osaka Suita\u2010shi Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4383-748X","authenticated-orcid":false,"given":"Shigeyuki","family":"Yagi","sequence":"additional","affiliation":[{"name":"Graduate School of Engineering Osaka Metropolitan University Sakai\u2010shi Osaka Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,5,18]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/0301\u20100104(94)00406\u2010Z"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molliq.2014.12.019"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.trac.2021.116189"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.2c04969"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2025.216602"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules30153084"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0645640"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja500280r"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.201102519"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/aenm.202000124"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102552"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/cm049679m"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/cm021056q"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201903269"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/cm7022136"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.200304486"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202102312"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.2c00087"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010021\u201024187\u20105"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/C2TC00175F"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/accountsmr.0c00114"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202310818"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biomaterials.2021.120717"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202007040"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1007\/s44211\u2010025\u201000735\u20107"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CS00307K"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12951\u2010022\u201001648\u20107"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsnano.4c14887"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2026.217598"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.talanta.2016.06.057"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsnano.9b08326"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00580"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100229a010"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/0301\u20100104(95)00017\u2010I"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4TB01592D"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200801918"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC06886B"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202404487"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202504564"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1007\/s41061\u2010024\u201000479\u20104"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.isci.2021.102858"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2021.109305"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/adom.202300989"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9TC05349B"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmaterialslett.3c00978"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmaterialslett.2c00451"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.mtchem.2024.102018"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpclett.3c02629"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/9780470142967.ch1"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-0-387-46312-4_6"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochem.2021.113164"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molliq.2024.126572"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100785a001"},{"key":"e_1_2_7_55_1","unstructured":"M. J.Frisch G. W.Trucks H. B.Schlegel et\u00a0al. Gaussian 09 Revision A.01 (Gaussian Inc. 2009)."},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00214\u2010007\u20100310\u2010x"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100096a001"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.3382344"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.22885"},{"key":"e_1_2_7_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemphys.2011.02.001"}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.70787","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/asia.70787","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.70787","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,12]],"date-time":"2026-07-12T06:36:02Z","timestamp":1783838162000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.70787"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,5]]},"references-count":59,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2026,5]]}},"alternative-id":["10.1002\/asia.70787"],"URL":"https:\/\/doi.org\/10.1002\/asia.70787","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"value":"1861-4728","type":"print"},{"value":"1861-471X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,5]]},"assertion":[{"value":"2026-02-08","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-05-05","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-05-18","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70787"}}