{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,11,9]],"date-time":"2026-11-09T13:31:15Z","timestamp":1794231075513,"version":"4.9.0"},"reference-count":52,"publisher":"American Chemical Society (ACS)","issue":"44","license":[{"start":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T00:00:00Z","timestamp":1792195200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T00:00:00Z","timestamp":1792195200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T00:00:00Z","timestamp":1792195200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE-2153081"],"award-info":[{"award-number":["CHE-2153081"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100007135","name":"University of Tennessee","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100007135","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100016204","name":"Minnesota Supercomputing Institute, University of Minnesota","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100016204","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100032787","name":"Muroran Institute of Technology","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100032787","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,11,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>BOPHYs are excellent fluorophores exhibiting high fluorescence quantum yield, strong visible light absorption, tunable emission colors, controllable electron-accepting properties, and high photostability. These properties make BOPHYs attractive as potential nonfullerene electron acceptors (NFAs). Recent studies on Y6, a benchmark NFA, have collectively suggested that charge-transfer character in the excited state promotes efficient charge generation. Here, the charge-transfer character in the excited state of a series of BOPHYs is investigated using electroabsorption and Stark fluorescence spectroscopies. Methyl-substituted, ester- and phenyl-substituted, and pyridone-fused BOPHYs are comparatively studied. Fluorescence quantum yield was reduced in the presence of electric fields, which was attributed primarily to an enhancement of intramolecular nonradiative deactivation processes. Time-dependent density functional theory (TD-DFT) calculations and analyses of electron density redistribution induced by photoexcitation indicate that molecular symmetry determines the patterns of local charge redistribution and consequently, the magnitude of the net dipole moment change (|\u03bc|). Among the three derivatives, pyridone-fused BOPHY exhibits the largest |\u03bc| upon photoexcitation. These results indicate that the lowest excited state of pyridone-fused BOPHY has substantial intramolecular charge-transfer character. This study provides a basis for the functionalization of BOPHY for future photovoltaic and organic optoelectronic applications in addition to the conventional \u03c0-conjugation extension approach.<\/jats:p>","DOI":"10.1021\/acs.inorgchem.6c03488","type":"journal-article","created":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T15:04:19Z","timestamp":1792249459000},"page":"25840-25850","source":"Crossref","is-referenced-by-count":0,"title":["Electroabsorption\nSpectroscopy of BOPHY Derivatives:\nProbing Charge-Transfer Character in the Excited State"],"prefix":"10.1021","volume":"65","author":[{"given":"Md Bulu","family":"Rahman","sequence":"first","affiliation":[{"name":"Muroran Institute of Technology , , Mizumoto-cho 27-1 , , ,","place":["Muroran, Hokkaido, Japan, 050-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Victoria","family":"Villarreal","sequence":"additional","affiliation":[{"name":"University of Tennessee , , , ,","place":["Knoxville, Tennessee, United States, 37996-1600"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dijo","family":"Prasannan","sequence":"additional","affiliation":[{"name":"University of Tennessee , , , ,","place":["Knoxville, Tennessee, United States, 37996-1600"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4345-0848","authenticated-orcid":true,"given":"Victor N.","family":"Nemykin","sequence":"additional","affiliation":[{"name":"University of Tennessee , , , ,","place":["Knoxville, Tennessee, United States, 37996-1600"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2158-4378","authenticated-orcid":true,"given":"Toshifumi","family":"Iimori","sequence":"additional","affiliation":[{"name":"Muroran Institute of Technology , , Mizumoto-cho 27-1 , , ,","place":["Muroran, Hokkaido, Japan, 050-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,17]]},"reference":[{"key":"2026110908152663300_cit1","doi-asserted-by":"publisher","first-page":"14180","DOI":"10.1021\/acs.chemrev.1c00955","article-title":"Renewed Prospects\nfor Organic Photovoltaics","volume":"122","author":"Zhang","year":"2022","journal-title":"Chem. 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Mater."},{"key":"2026110908152663300_cit5","doi-asserted-by":"publisher","first-page":"1140","DOI":"10.1016\/j.joule.2019.01.004","article-title":"Single-Junction Organic\nSolar Cell with over 15% Efficiency\nUsing Fused-Ring Acceptor with Electron-Deficient Core","volume":"3","author":"Yuan","year":"2019","journal-title":"Joule"},{"key":"2026110908152663300_cit6","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-46462-x","article-title":"Assessing Intra-\nand Inter-Molecular Charge Transfer Excitations in Non-Fullerene Acceptors\nUsing Electroabsorption Spectroscopy","volume":"15","author":"Mahadevan","year":"2024","journal-title":"Nat. Commun."},{"key":"2026110908152663300_cit7","doi-asserted-by":"publisher","first-page":"12751","DOI":"10.1021\/jacs.0c04890","article-title":"Charge Separation from\nan Intra-Moiety Intermediate State in the\nHigh-Performance Pm6:Y6 Organic Photovoltaic Blend","volume":"142","author":"Wang","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"2026110908152663300_cit8","doi-asserted-by":"publisher","first-page":"1295","DOI":"10.1021\/jacsau.4c00046","article-title":"New Avenues for Organic Solar Cells\nUsing Intrinsically Charge-Generating Materials","volume":"4","author":"Hume","year":"2024","journal-title":"JACS Au"},{"key":"2026110908152663300_cit9","doi-asserted-by":"publisher","first-page":"1367","DOI":"10.1021\/acs.jpclett.4c03119","article-title":"Morphological Control of Y6 Thin Films Reveals Charge\nTransfer Is Facilitated by Co-Facial Interactions","volume":"16","author":"Kumar","year":"2025","journal-title":"J. Phys. Chem. Lett."},{"key":"2026110908152663300_cit10","doi-asserted-by":"publisher","first-page":"10595","DOI":"10.1021\/acs.jpclett.1c03365","article-title":"Direct Observation of the Charge Transfer States from\na Non-Fullerene Organic Solar Cell with a Small Driving Force","volume":"12","author":"Wan","year":"2021","journal-title":"J. Phys. Chem. Lett."},{"key":"2026110908152663300_cit11","doi-asserted-by":"publisher","first-page":"1288","DOI":"10.1021\/acs.jpclett.3c03262","article-title":"Probing Charge Transfer Character\nin Modern Donor\/Acceptor\nMaterials Via Electroabsorption Spectroscopy","volume":"15","author":"Bothra","year":"2024","journal-title":"J. Phys. Chem. Lett."},{"key":"2026110908152663300_cit12","doi-asserted-by":"publisher","first-page":"2468","DOI":"10.1021\/acs.inorgchem.4c04972","article-title":"Introducing Pyridone[\u03b1]-Fused\nBOPHYs as Red-Shifted\nBright Fluorophore Potentially Useful as Non-Fullerene Acceptors in\nDonor\u2013Acceptor Dyads","volume":"64","author":"Prasannan","year":"2025","journal-title":"Inorg. Chem."},{"key":"2026110908152663300_cit13","doi-asserted-by":"publisher","first-page":"12320","DOI":"10.1021\/acs.orglett.5c03888","article-title":"Synthesis\nand Ultrafast Intramolecular Energy Transfer in BODIPY\/Porphyrin-BOPHY\nDyads","volume":"27","author":"Prasannan","year":"2025","journal-title":"Org. Lett."},{"key":"2026110908152663300_cit14","doi-asserted-by":"publisher","first-page":"5623","DOI":"10.1021\/ja502477a","article-title":"A New Highly\nFluorescent and Symmetric Pyrrole\u2013BF2 Chromophore:\nBOPHY","volume":"136","author":"Tamgho","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"2026110908152663300_cit15","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.ccr.2018.05.011","article-title":"The BOPHY Fluorophore\nwith Double Boron Chelation: Synthesis and Spectroscopy","volume":"371","author":"Boodts","year":"2018","journal-title":"Coord. Chem. Rev."},{"key":"2026110908152663300_cit16","doi-asserted-by":"publisher","first-page":"1569","DOI":"10.1039\/D0DT03964K","article-title":"Synthesis Pathways\nfor the Preparation\nof the BODIPY Analogues: aza-BODIPYs, BOPHYs and Some Other Pyrrole-based\nAcyclic Chromophores","volume":"50","author":"Shamova","year":"2021","journal-title":"Dalton Trans."},{"key":"2026110908152663300_cit17","doi-asserted-by":"publisher","first-page":"1134","DOI":"10.1021\/acs.joc.7b02415","article-title":"Polybrominated\nBOPHY Dyes: Synthesis, Reactivity, and Properties","volume":"83","author":"Lv","year":"2018","journal-title":"J. Org. Chem."},{"key":"2026110908152663300_cit18","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2024.215892","article-title":"Synthesis, Properties and Emerging Applications of Multi-Boron Coordinated\nChromophores","volume":"513","author":"Jin","year":"2024","journal-title":"Coord. Chem. 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J."},{"key":"2026110908152663300_cit21","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2019.107662","article-title":"BOPHYs versus\nBODIPYs: A Comparison of Their Performance as Effective Multi-Function\nOrganic Dyes","volume":"170","author":"Sola-Llano","year":"2019","journal-title":"Dyes Pigm."},{"key":"2026110908152663300_cit22","doi-asserted-by":"publisher","DOI":"10.3389\/fchem.2022.921112","article-title":"Hybridising\nInorganic Materials with Fluorescent BOPHY\nDyes: A Structural and Optical Comparative Study","volume":"10","author":"Sani","year":"2022","journal-title":"Front. Chem."},{"key":"2026110908152663300_cit23","doi-asserted-by":"publisher","first-page":"10850","DOI":"10.1021\/acs.jpcb.7b09698","article-title":"Combined Td-Dft-Sos-Cis(D)\nStudy of BOPHY Derivatives with Potential Application in Biosensing","volume":"121","author":"Ponce-Vargas","year":"2017","journal-title":"J. Phys. Chem. B"},{"key":"2026110908152663300_cit24","doi-asserted-by":"publisher","first-page":"33","DOI":"10.1016\/j.snb.2016.05.055","article-title":"A BOPHY Probe for the\nFluorescence Turn-on Detection of Cu2+","volume":"235","author":"Li","year":"2016","journal-title":"Sens. Actuators, B"},{"key":"2026110908152663300_cit25","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2023.135118","article-title":"Synthesis\nof Selenium-Based BOPHY Sensor for Imaging of Cu(II) in Living Hela\nCells","volume":"1281","author":"Malankar","year":"2023","journal-title":"J. Mol. Struct."},{"key":"2026110908152663300_cit26","doi-asserted-by":"publisher","DOI":"10.1016\/j.aca.2021.338205","article-title":"Organoselenium-Based\nBOPHY as a Sensor for Detection\nof Hypochlorous Acid in Mammalian Cells","volume":"1150","author":"Malankar","year":"2021","journal-title":"Anal.\nChim. Acta"},{"key":"2026110908152663300_cit27","doi-asserted-by":"publisher","first-page":"16735","DOI":"10.1039\/C4RA15914D","article-title":"Synthesis of Mono-(P-Dimethylamino)Styryl-Containing\nBOPHY Dye for a Turn-on Ph Sensor","volume":"5","author":"Jiang","year":"2015","journal-title":"RSC Adv."},{"key":"2026110908152663300_cit28","doi-asserted-by":"publisher","first-page":"10069","DOI":"10.1039\/D2DT01086K","article-title":"A BOPHY Based Fluorescent\nProbe for Hg2+Via NTe2 Chelation","volume":"51","author":"Malankar","year":"2022","journal-title":"Dalton Trans."},{"key":"2026110908152663300_cit29","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202304490","article-title":"An Unprecedented\nReaction of BOPHY:\nFluorimetric Chemosensing of Amines by Tetrabrominated BOPHY","volume":"9","author":"Tunca","year":"2024","journal-title":"ChemistrySelect"},{"key":"2026110908152663300_cit30","doi-asserted-by":"publisher","DOI":"10.1002\/cptc.202400077","article-title":"BOPHY Derivatives\nas Phototherapeutic Agents for the Photodynamic Inactivation of Microorganisms","volume":"8","author":"Herna\u0301ndez","year":"2024","journal-title":"ChemPhotoChem"},{"key":"2026110908152663300_cit31","doi-asserted-by":"publisher","first-page":"1623","DOI":"10.1039\/C5TC03193A","article-title":"Triplet Excited State of DiiodoBOPHY Derivatives: Preparation, Study\nof Photophysical Properties and Application in Triplet\u2013Triplet\nAnnihilation Upconversion","volume":"4","author":"Zhang","year":"2016","journal-title":"J. Mater. Chem. C"},{"key":"2026110908152663300_cit32","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcatb.2019.117933","article-title":"Conjugated Porous Polymer\nBased on BOPHY Dyes as Photocatalyst under Visible Light","volume":"258","author":"Lo\u0301pez-Calixto","year":"2019","journal-title":"Appl. Catal., B"},{"key":"2026110908152663300_cit33","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202403778","article-title":"High-Performance\nMicrofluidic Techniques\ntoward Nanostructuration of BODIPY and BOPHY Based CPPs Hybrid Photocatalyst\nfor Hydrogen Production","volume":"34","author":"Palenzuela-Rebella","year":"2024","journal-title":"Adv. Funct. Mater."},{"key":"2026110908152663300_cit34","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202105384","article-title":"Conjugated\nPorous Polymers Based\non BODIPY and BOPHY Dyes in Hybrid Heterojunctions for Artificial\nPhotosynthesis","volume":"31","author":"Collado","year":"2021","journal-title":"Adv. Funct. Mater."},{"key":"2026110908152663300_cit35","doi-asserted-by":"publisher","first-page":"750","DOI":"10.1039\/c8pp00162f","article-title":"Photocatalysis and\nSelf-Catalyzed Photobleaching with Covalently-Linked Chromophore-Quencher\nConjugates Built around BOPHY","volume":"17","author":"Sirbu","year":"2018","journal-title":"Photochem. Photobiol.\nSci."},{"key":"2026110908152663300_cit36","doi-asserted-by":"publisher","first-page":"14742","DOI":"10.1039\/C5CC05095B","article-title":"Thienyl-BOPHY Dyes\nas Promising Templates for Bulk Heterojunction Solar Cells","volume":"51","author":"Mirloup","year":"2015","journal-title":"Chem. Commun."},{"key":"2026110908152663300_cit37","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202200421","article-title":"Investigations on the Synthesis, Reactivity, and Properties\nof Perfluoro-\u0391-Benzo-Fused BOPHY Fluorophores","volume":"28","author":"Zhang","year":"2022","journal-title":"Chem. - Eur. J."},{"key":"2026110908152663300_cit38","doi-asserted-by":"publisher","first-page":"4307","DOI":"10.1021\/acs.jpca.6b02625","article-title":"Stark Spectroscopy of Rubrene. I.\nElectroabsorption Spectroscopy and Molecular Parameters","volume":"120","author":"Iimori","year":"2016","journal-title":"J. Phys. Chem. A"},{"key":"2026110908152663300_cit39","doi-asserted-by":"publisher","first-page":"2972","DOI":"10.1021\/jp8067393","article-title":"Stark Realities","volume":"113","author":"Boxer","year":"2009","journal-title":"J. Phys. Chem.\nB"},{"key":"2026110908152663300_cit40","doi-asserted-by":"publisher","first-page":"1637","DOI":"10.1246\/bcsj.75.1637","article-title":"Electric Field\nEffects on Photochemical Dynamics in Solid Films","volume":"75","author":"Ohta","year":"2002","journal-title":"Bull. Chem. Soc. 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Chem. Lett."},{"key":"2026110908152663300_cit44","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-024-81957-z","article-title":"Excited States of Mono- and Biruthenium(Ii)\nComplexes\nAdsorbed on Nanocrystalline Titanium Dioxide Studied by Electroabsorption\nSpectroscopy","volume":"15","author":"Pelczarski","year":"2025","journal-title":"Sci. Rep."},{"key":"2026110908152663300_cit45","doi-asserted-by":"publisher","first-page":"6644","DOI":"10.1021\/acs.jpca.5c03562","article-title":"Electroabsorbance\nand Electrofluorescence Analysis of 1,7-, 1,6-, and 1,6,7- Derivatives\nof Dodecylthio Perylene Diimides","volume":"129","author":"Dinolfo","year":"2025","journal-title":"J. Phys. Chem.\nA"},{"key":"2026110908152663300_cit46","doi-asserted-by":"publisher","first-page":"21317","DOI":"10.1039\/D3CP01669B","article-title":"Charge-Transfer State and State Mixing\nin Tetracyanoquinodimethane Probed Using Electroabsorption Spectroscopy","volume":"25","author":"Islam","year":"2023","journal-title":"Phys. Chem. Chem. Phys."},{"key":"2026110908152663300_cit47","doi-asserted-by":"publisher","first-page":"5497","DOI":"10.1021\/acs.jpca.6b02627","article-title":"Stark Spectroscopy of Rubrene. II. Stark Fluorescence\nSpectroscopy and Fluorescence Quenching Induced by an External Electric\nField","volume":"120","author":"Iimori","year":"2016","journal-title":"J. Phys. Chem. A"},{"key":"2026110908152663300_cit48","first-page":"129","article-title":"Dipole Moments\nand Polarizabilities of Molecules in Excited Electronic States","volume-title":"Excited States","author":"Liptay","year":"1974"},{"key":"2026110908152663300_cit49","doi-asserted-by":"publisher","first-page":"3365","DOI":"10.1021\/ja9640814","article-title":"Stark Spectroscopy\nof Donor\/Acceptor Substituted Polyenes","volume":"119","author":"Bublitz","year":"1997","journal-title":"J. Am.\nChem. Soc."},{"key":"2026110908152663300_cit50","doi-asserted-by":"publisher","first-page":"166","DOI":"10.1016\/j.ccr.2015.03.027","article-title":"Exploring\nExcited States Using Time Dependent Density\nFunctional Theory and Density-Based Indexes","volume":"304\u2013305","author":"Adamo","year":"2015","journal-title":"Coord. Chem. Rev."},{"key":"2026110908152663300_cit51","doi-asserted-by":"publisher","first-page":"1828","DOI":"10.1021\/acs.jpclett.9b00751","article-title":"Rapid Excited-State Deactivation\nof Bodipy Derivatives\nby a Boron-Bound Catechol","volume":"10","author":"Swedin","year":"2019","journal-title":"J. Phys. Chem. Lett."},{"key":"2026110908152663300_cit52","doi-asserted-by":"publisher","first-page":"2349","DOI":"10.1039\/C4CP04737K","article-title":"Ultrafast\nDynamics of a New Class of Highly Fluorescent Boron Difluoride Dyes","volume":"17","author":"Wang","year":"2015","journal-title":"Phys. Chem. Chem. Phys."}],"container-title":["Inorganic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.inorgchem.6c03488","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/inocaj\/article-pdf\/65\/44\/25840\/68895969\/acs.inorgchem.6c03488.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/inocaj\/article-pdf\/65\/44\/25840\/68895969\/acs.inorgchem.6c03488.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,11,9]],"date-time":"2026-11-09T13:15:34Z","timestamp":1794230134000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/inocaj\/article\/65\/44\/25840\/5453259\/Electroabsorption-Spectroscopy-of-BOPHY"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,17]]},"references-count":52,"journal-issue":{"issue":"44","published-online":{"date-parts":[[2026,10,17]]},"published-print":{"date-parts":[[2026,11,9]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.inorgchem.6c03488","relation":{"has-part":[{"id-type":"doi","id":"https:\/\/doi.org\/10.1021\/acs.inorgchem.6c03488.s001","asserted-by":"subject"}]},"ISSN":["0020-1669","1520-510X"],"issn-type":[{"value":"0020-1669","type":"print"},{"value":"1520-510X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,17]]}}}