{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T05:37:50Z","timestamp":1788932270651,"version":"build-2803163510"},"reference-count":92,"publisher":"American Chemical Society (ACS)","issue":"40","license":[{"start":{"date-parts":[[2023,10,3]],"date-time":"2023-10-03T00:00:00Z","timestamp":1696291200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2023,10,3]],"date-time":"2023-10-03T00:00:00Z","timestamp":1696291200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2023,10,3]],"date-time":"2023-10-03T00:00:00Z","timestamp":1696291200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100006151","name":"Basic Energy Sciences","doi-asserted-by":"publisher","award":["DE-AC02-06CH11357"],"award-info":[{"award-number":["DE-AC02-06CH11357"]}],"id":[{"id":"10.13039\/100006151","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100006151","name":"Basic Energy Sciences","doi-asserted-by":"publisher","award":["DE-SC0012704"],"award-info":[{"award-number":["DE-SC0012704"]}],"id":[{"id":"10.13039\/100006151","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100006151","name":"Basic Energy Sciences","doi-asserted-by":"publisher","award":["DE-SC0022036"],"award-info":[{"award-number":["DE-SC0022036"]}],"id":[{"id":"10.13039\/100006151","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100015895","name":"Centre of Excellence in Exciton Science","doi-asserted-by":"publisher","award":["CE170100026"],"award-info":[{"award-number":["CE170100026"]}],"id":[{"id":"10.13039\/501100015895","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100014037","name":"National Defense Science and Engineering Graduate","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100014037","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Lindemann Trust Fellowship"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2023,10,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The evolution of molecular platforms for singlet fission (SF) chromophores has fueled the quest for new compounds capable of generating triplets quantitatively at fast time scales. As the exploration of molecular motifs for SF has diversified, a key challenge has emerged in identifying when the criteria for SF have been satisfied. Here, we show how covalently bound molecular dimers uniquely provide a set of characteristic optical markers that can be used to distinguish triplet pair formation from processes that generate an individual triplet. These markers are contained within (i) triplet charge-transfer excited state absorption features, (ii) kinetic signatures of triplet\u2013triplet annihilation processes, and (iii) the modulation of triplet formation rates using bridging moieties between chromophores. Our assignments are verified by time-resolved electron paramagnetic resonance (EPR) measurements, which directly identify triplet pairs by their electron spin and polarization patterns. We apply these diagnostic criteria to dimers of acenothiophene derivatives in solution that were recently reported to undergo efficient intermolecular SF in condensed media. While the electronic structure of these heteroatom-containing chromophores can be broadly tuned, the effect of their enhanced spin\u2013orbit coupling and low-energy nonbonding orbitals on their SF dynamics has not been fully determined. We find that SF is fast and efficient in tetracenothiophene but that anthradithiophene exhibits fast intersystem crossing due to modifications of the singlet and triplet excited state energies upon functionalization of the heterocycle. We conclude that it is not sufficient to assign SF based on comparisons of the triplet formation kinetics between monomer and multichromophore systems.<\/jats:p>","DOI":"10.1021\/jacs.3c07082","type":"journal-article","created":{"date-parts":[[2023,10,3]],"date-time":"2023-10-03T08:18:26Z","timestamp":1696321106000},"page":"22058-22068","source":"Crossref","is-referenced-by-count":19,"title":["Unraveling Triplet\nFormation Mechanisms in Acenothiophene\nChromophores"],"prefix":"10.1021","volume":"145","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4009-2590","authenticated-orcid":true,"given":"Guiying","family":"He","sequence":"first","affiliation":[{"name":"City University of New York , , , ,","place":["New York, New York, United States, 10016"]},{"name":"City University of New York , , , ,","place":["New York, New York, United States, 10031"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4001-3952","authenticated-orcid":true,"given":"Kaia R.","family":"Parenti","sequence":"additional","affiliation":[{"name":"Columbia University , , , ,","place":["New York, New York, United States, 10027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter J.","family":"Budden","sequence":"additional","affiliation":[{"name":"City University of New York , , , ,","place":["New York, New York, United States, 10016"]},{"name":"City University of New York , , , ,","place":["New York, New York, United States, 10031"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6462-2680","authenticated-orcid":true,"given":"Jens","family":"Niklas","sequence":"additional","affiliation":[{"name":"Argonne National Laboratory , , , ,","place":["Lemont, Illinois, United States, 60439"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2219-6759","authenticated-orcid":true,"given":"Thomas","family":"Macdonald","sequence":"additional","affiliation":[{"name":"UNSW Sydney , , , ,","place":["Sydney, NSW, Australia, 2052"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7995-6894","authenticated-orcid":true,"given":"Elango","family":"Kumarasamy","sequence":"additional","affiliation":[{"name":"Columbia University , , , ,","place":["New York, New York, United States, 10027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xing","family":"Chen","sequence":"additional","affiliation":[{"name":"Beijing Institute of Technology , , ,","place":["Beijing, P. R. China, 102488"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7644-6744","authenticated-orcid":true,"given":"Xiaodong","family":"Yin","sequence":"additional","affiliation":[{"name":"Beijing Institute of Technology , , ,","place":["Beijing, P. R. China, 102488"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dane R.","family":"McCamey","sequence":"additional","affiliation":[{"name":"UNSW Sydney , , , ,","place":["Sydney, NSW, Australia, 2052"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3067-9272","authenticated-orcid":true,"given":"Oleg G.","family":"Poluektov","sequence":"additional","affiliation":[{"name":"Argonne National Laboratory , , , ,","place":["Lemont, Illinois, United States, 60439"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2110-2666","authenticated-orcid":true,"given":"Luis M.","family":"Campos","sequence":"additional","affiliation":[{"name":"Columbia University , , , ,","place":["New York, New York, United States, 10027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5619-5722","authenticated-orcid":true,"given":"Matthew Y.","family":"Sfeir","sequence":"additional","affiliation":[{"name":"City University of New York , , , ,","place":["New York, New York, United States, 10016"]},{"name":"City University of New York , , , ,","place":["New York, New York, United States, 10031"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2023,10,3]]},"reference":[{"issue":"6698","key":"2026081707192503800_cit1","doi-asserted-by":"publisher","first-page":"151","DOI":"10.1038\/25954","article-title":"Highly Efficient\nPhosphorescent Emission from Organic Electroluminescent Devices","volume":"395","author":"Baldo","year":"1998","journal-title":"Nature"},{"issue":"6427","key":"2026081707192503800_cit2","doi-asserted-by":"publisher","first-page":"601","DOI":"10.1126\/science.aav2865","article-title":"Eliminating\nNonradiative Decay in\nCu\u00ad(I) Emitters: &gt;99% Quantum Efficiency and Microsecond Lifetime","volume":"363","author":"Hamze","year":"2019","journal-title":"Science"},{"issue":"10","key":"2026081707192503800_cit3","doi-asserted-by":"publisher","first-page":"5048","DOI":"10.1063\/1.1409582","article-title":"Nearly 100% Internal\nPhosphorescence Efficiency in an Organic Light-Emitting Device","volume":"90","author":"Adachi","year":"2001","journal-title":"J. Appl. Phys."},{"issue":"7428","key":"2026081707192503800_cit4","doi-asserted-by":"publisher","first-page":"234","DOI":"10.1038\/nature11687","article-title":"Highly Efficient\nOrganic Light-Emitting Diodes from Delayed Fluorescence","volume":"492","author":"Uoyama","year":"2012","journal-title":"Nature"},{"issue":"3","key":"2026081707192503800_cit5","doi-asserted-by":"publisher","first-page":"915","DOI":"10.1039\/C6CS00368K","article-title":"Recent Advances in Organic Thermally\nActivated Delayed Fluorescence Materials","volume":"46","author":"Yang","year":"2017","journal-title":"Chem.\nSoc. Rev."},{"issue":"4","key":"2026081707192503800_cit6","doi-asserted-by":"publisher","first-page":"326","DOI":"10.1038\/nphoton.2014.12","article-title":"Efficient\nBlue Organic Light-Emitting Diodes Employing Thermally Activated Delayed\nFluorescence","volume":"8","author":"Zhang","year":"2014","journal-title":"Nat. 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Mater."},{"issue":"28","key":"2026081707192503800_cit21","doi-asserted-by":"publisher","first-page":"8965","DOI":"10.1021\/jacs.5b04986","article-title":"Quantitative\nIntramolecular Singlet Fission in Bipentacenes","volume":"137","author":"Sanders","year":"2015","journal-title":"J. Am. Chem. Soc."},{"issue":"3","key":"2026081707192503800_cit22","doi-asserted-by":"publisher","first-page":"505","DOI":"10.1016\/j.chempr.2016.08.016","article-title":"Singlet\nFission in Polypentacene","volume":"1","author":"Sanders","year":"2016","journal-title":"Chem"},{"issue":"2","key":"2026081707192503800_cit23","doi-asserted-by":"publisher","first-page":"163","DOI":"10.1038\/s41557-020-00593-y","article-title":"Emissive Spin-0 Triplet-Pairs\nAre a Direct Product of Triplet\u2013Triplet Annihilation in Pentacene\nSingle Crystals and Anthradithiophene Films","volume":"13","author":"Bossanyi","year":"2021","journal-title":"Nat. Chem."},{"issue":"11","key":"2026081707192503800_cit24","doi-asserted-by":"publisher","first-page":"6891","DOI":"10.1021\/cr1002613","article-title":"Singlet Fission","volume":"110","author":"Smith","year":"2010","journal-title":"Chem. Rev."},{"issue":"1","key":"2026081707192503800_cit25","doi-asserted-by":"publisher","first-page":"361","DOI":"10.1146\/annurev-physchem-040412-110130","article-title":"Recent Advances in Singlet Fission","volume":"64","author":"Smith","year":"2013","journal-title":"Annu. Rev.\nPhys. Chem."},{"issue":"11","key":"2026081707192503800_cit26","doi-asserted-by":"publisher","first-page":"17063","DOI":"10.1038\/natrevmats.2017.63","article-title":"Harnessing Singlet\nExciton Fission to Break the Shockley\u2013Queisser\nLimit","volume":"2","author":"Rao","year":"2017","journal-title":"Nat. Rev. Mater."},{"issue":"6","key":"2026081707192503800_cit27","doi-asserted-by":"publisher","first-page":"4261","DOI":"10.1021\/acs.chemrev.8b00572","article-title":"Triplet Pair States\nin Singlet Fission","volume":"119","author":"Miyata","year":"2019","journal-title":"Chem. Rev."},{"issue":"9","key":"2026081707192503800_cit28","doi-asserted-by":"publisher","first-page":"821","DOI":"10.1038\/s41557-019-0297-7","article-title":"Ultra-Fast\nIntramolecular Singlet Fission to Persistent Multiexcitons by Molecular\nDesign","volume":"11","author":"Pun","year":"2019","journal-title":"Nat. Chem."},{"issue":"40","key":"2026081707192503800_cit29","doi-asserted-by":"publisher","DOI":"10.1002\/adma.202203974","article-title":"Direct Exciton Harvesting\nfrom a Bound Triplet Pair","volume":"34","author":"He","year":"2022","journal-title":"Adv. Mater."},{"issue":"34","key":"2026081707192503800_cit30","doi-asserted-by":"publisher","first-page":"15509","DOI":"10.1021\/jacs.2c03550","article-title":"Effects of the Separation Distance\nbetween Two Triplet States Produced from Intramolecular Singlet Fission\non the Two-Electron-Transfer Process","volume":"144","author":"Liu","year":"2022","journal-title":"J. Am.\nChem. Soc."},{"issue":"2","key":"2026081707192503800_cit31","doi-asserted-by":"publisher","first-page":"182","DOI":"10.1038\/nphys3909","article-title":"Quintet Multiexciton Dynamics in Singlet Fission","volume":"13","author":"Tayebjee","year":"2017","journal-title":"Nat. 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Soc."},{"issue":"35","key":"2026081707192503800_cit34","doi-asserted-by":"publisher","first-page":"13867","DOI":"10.1021\/jacs.9b06346","article-title":"Exploiting\nExcited-State Aromaticity To Design Highly Stable Singlet Fission\nMaterials","volume":"141","author":"Fallon","year":"2019","journal-title":"J. Am. Chem. Soc."},{"issue":"23","key":"2026081707192503800_cit35","doi-asserted-by":"publisher","first-page":"10235","DOI":"10.1021\/jacs.0c00089","article-title":"Singlet Fission\nin a Pyrrole-Fused Cross-Conjugated\nSkeleton with Adaptive Aromaticity","volume":"142","author":"Wang","year":"2020","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026081707192503800_cit36","doi-asserted-by":"publisher","first-page":"12276","DOI":"10.1021\/acs.jpclett.1c03265","article-title":"H-Type-like Aggregation-Accelerated\nSinglet Fission Process in Dipyrrolonaphthyridinedione Thin Film:\nThe Role of Charge Transfer\/Excimer Mixed Intermediate State","volume":"12","author":"Wang","year":"2021","journal-title":"J. Phys. Chem. Lett."},{"issue":"45","key":"2026081707192503800_cit37","doi-asserted-by":"publisher","first-page":"8596","DOI":"10.1021\/acs.jpca.7b07362","article-title":"Singlet Fission\nand Excimer Formation\nin Disordered Solids of Alkyl-Substituted 1,3-Diphenylisobenzofurans","volume":"121","author":"Dron","year":"2017","journal-title":"J. Phys. Chem. A"},{"issue":"2","key":"2026081707192503800_cit38","doi-asserted-by":"publisher","first-page":"145","DOI":"10.1021\/jz2015346","article-title":"Diradical Character\nView of Singlet Fission","volume":"3","author":"Minami","year":"2012","journal-title":"J. Phys. Chem. Lett."},{"issue":"50","key":"2026081707192503800_cit39","doi-asserted-by":"publisher","first-page":"18376","DOI":"10.1021\/jacs.7b10762","article-title":"Efficient Singlet\nFission and Triplet-Pair\nEmission in a Family of Zethrene Diradicaloids","volume":"139","author":"Lukman","year":"2017","journal-title":"J. Am. Chem. Soc."},{"issue":"20","key":"2026081707192503800_cit40","doi-asserted-by":"publisher","first-page":"7363","DOI":"10.1021\/ja501337b","article-title":"Mechanism of Singlet\nFission in Thin Films of 1,3-Diphenylisobenzofuran","volume":"136","author":"Schrauben","year":"2014","journal-title":"J. Am. Chem. Soc."},{"issue":"42","key":"2026081707192503800_cit41","doi-asserted-by":"publisher","first-page":"17892","DOI":"10.1021\/jacs.0c06604","article-title":"Singlet Fission\nin a Para -Azaquinodimethane-Based Quinoidal Conjugated\nPolymer","volume":"142","author":"Wang","year":"2020","journal-title":"J. Am. Chem. Soc."},{"issue":"17","key":"2026081707192503800_cit42","doi-asserted-by":"publisher","first-page":"6159","DOI":"10.1039\/D1SC00382H","article-title":"Excited State Character\nof Cibalackrot-Type Compounds\nInterpreted in Terms of Hu\u0308ckel-Aromaticity: A Rationale for\nSinglet Fission Chromophore Design","volume":"12","author":"Zeng","year":"2021","journal-title":"Chem. Sci."},{"issue":"25","key":"2026081707192503800_cit43","doi-asserted-by":"publisher","first-page":"10287","DOI":"10.1021\/acs.jpcc.2c02298","article-title":"Effect\nof Crystallinity on Endoergic Singlet Fission in Perylenediimide Single\nCrystals and Polycrystalline Films","volume":"126","author":"Williams","year":"2022","journal-title":"J. Phys.\nChem. C"},{"issue":"2","key":"2026081707192503800_cit44","doi-asserted-by":"publisher","first-page":"814","DOI":"10.1021\/jacs.7b11888","article-title":"Singlet Fission Involves an Interplay\nbetween Energetic\nDriving Force and Electronic Coupling in Perylenediimide Films","volume":"140","author":"Le","year":"2018","journal-title":"J. Am. Chem. Soc."},{"issue":"30","key":"2026081707192503800_cit45","doi-asserted-by":"publisher","first-page":"5700","DOI":"10.1021\/jp503114b","article-title":"Effects of\nHeteroatoms of Tetracene\nand Pentacene Derivatives on Their Stability and Singlet Fission","volume":"118","author":"Chen","year":"2014","journal-title":"J. Phys. Chem. A"},{"issue":"6","key":"2026081707192503800_cit46","doi-asserted-by":"publisher","first-page":"1676","DOI":"10.1021\/acs.accounts.5b00118","article-title":"The\nLarger Linear N-Heteroacenes","volume":"48","author":"Bunz","year":"2015","journal-title":"Acc. Chem. 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