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Metal-Free Organic Triplet Emitters with On–Off Switchable Excited State Intramolecular Proton Transfer
dc.contributor.authorShao, Wenhao
dc.contributor.authorHao, Jie
dc.contributor.authorJiang, Hanjie
dc.contributor.authorZimmerman, Paul M.
dc.contributor.authorKim, Jinsang
dc.date.accessioned2022-08-02T18:56:36Z
dc.date.available2023-08-02 14:56:34en
dc.date.available2022-08-02T18:56:36Z
dc.date.issued2022-07
dc.identifier.citationShao, Wenhao; Hao, Jie; Jiang, Hanjie; Zimmerman, Paul M.; Kim, Jinsang (2022). "Metal-Free Organic Triplet Emitters with On–Off Switchable Excited State Intramolecular Proton Transfer." Advanced Functional Materials 32(29): n/a-n/a.
dc.identifier.issn1616-301X
dc.identifier.issn1616-3028
dc.identifier.urihttps://hdl.handle.net/2027.42/173091
dc.description.abstractMetal-free organic triplet emitters are an emerging class of organic semiconducting material. Among them, molecules with tunable emission responsive to environmental stimuli have shown great potential in solid-state lighting, sensors, and anti-counterfeiting systems. Here, a novel excited-state intramolecular proton transfer (ESIPT) system is proposed showing the activation of thermally activated delayed fluorescence (TADF) or room-temperature phosphorescence (RTP) simultaneously from both keto and enol tautomers. The prototype ESIPT triplet emitters exhibit up to 50% delayed emission quantum yield. Their enol–keto tautomerization can be switched by controlling the matrix acidity in doped polymer films. Taking advantage of these unique properties, “on-off” switchable triplet emission systems controlled by acid vapor annealing, as well as photopatterning systems capable of generating facile and high-contrast emissive patterns, are devised.A novel excited-state intramolecular proton transfer (ESIPT) system is presented exhibiting thermally activated delayed fluorescence or room-temperature phosphorescence simultaneously from keto or enol tautomers, respectively. These ESIPT triplet emitters show up to 50% delayed emission quantum yield and acidity-responsive switchable tautomerization. Unique “on-off” switchable triplet emission controlled by acid vapor annealing as well as high-contrast photopatterning systems is demonstrated.
dc.publisherUniversity Science Books
dc.publisherWiley Periodicals, Inc.
dc.subject.otherexcited-state intramolecular proton transfer
dc.subject.otherthermally activated delayed fluorescence
dc.subject.otherswitchable triplet emission systems
dc.subject.otherroom-temperature phosphorescence
dc.subject.othermetal-free organic triplet emitters
dc.titleMetal-Free Organic Triplet Emitters with On–Off Switchable Excited State Intramolecular Proton Transfer
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelEngineering (General)
dc.subject.hlbsecondlevelMaterials Science and Engineering
dc.subject.hlbtoplevelEngineering
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/173091/1/adfm202201256-sup-0001-SuppMat.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/173091/2/adfm202201256_am.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/173091/3/adfm202201256.pdf
dc.identifier.doi10.1002/adfm.202201256
dc.identifier.sourceAdvanced Functional Materials
dc.identifier.citedreferenceH. Ma, Q. Peng, Z. An, W. Huang, Z. Shuai, J. Am. Chem. Soc. 2019, 141, 1010.
dc.identifier.citedreferenceN. A. Kukhta, M. R. Bryce, Mater. Horiz. 2021, 8, 33.
dc.identifier.citedreferenceV. S. Padalkar, S. Seki, Chem. Soc. Rev. 2016, 45, 169.
dc.identifier.citedreferenceD. McMorrow, M. Kasha, J. Am. Chem. Soc. 1983, 105, 5133.
dc.identifier.citedreferenceM. Kasha, J. Chem. Soc., Faraday Trans. 2 1986, 82, 2379.
dc.identifier.citedreferenceM. H. van Benthem, G. D. Gillispie, J. Phys. Chem. 1984, 88, 2954.
dc.identifier.citedreferenceJ. Massue, D. Jacquemin, G. Ulrich, Chem. Lett. 2018, 47, 1083.
dc.identifier.citedreferenceS. Mukherjee, P. Thilagar, Chem. Commun. 2015, 51, 10988.
dc.identifier.citedreferenceM. Hagiri, N. Ichinose, J. I. Kinugasa, T. Iwasa, T. Nakayama, Chem. Lett. 2004, 33, 326.
dc.identifier.citedreferenceH. Saigusa, T. Azumi, J. Chem. Phys. 2008, 71, 1408.
dc.identifier.citedreferenceM. A. El-Sayed, J. Chem. Phys. 1963, 38, 2834.
dc.identifier.citedreferenceN. J. Turro, V. Ramamurthy, J. C. Scaiano, Modern Molecular Photochemistry of Organic Molecules, First Indi., Vol. 88, University Science Books, Sausalito, CA 2012.
dc.identifier.citedreferenceW. Shao, H. Jiang, R. Ansari, P. Zimmerman, J. Kim, Chem. Sci. 2022, 13, 789.
dc.identifier.citedreferenceA. D. Chien, P. M. Zimmerman, J. Chem. Phys. 2017, 146, 014103.
dc.identifier.citedreferenceF. Bell, P. M. Zimmerman, D. Casanova, M. Goldey, M. Head-Gordon, Phys. Chem. Chem. Phys. 2013, 15, 358.
dc.identifier.citedreferenceP. M. Zimmerman, F. Bell, M. Goldey, A. T. Bell, M. Head-Gordon, J. Chem. Phys. 2012, 137, 164110.
dc.identifier.citedreferenceH. Jiang, P. M. Zimmerman, J. Chem. Phys. 2020, 153, 064109.
dc.identifier.citedreferenceD. Casanova, M. Head-Gordon, Phys. Chem. Chem. Phys. 2009, 11, 9779.
dc.identifier.citedreferenceA. I. Krylov, Chem. Phys. Lett. 2001, 338, 375.
dc.identifier.citedreferenceA. I. Krylov, Chem. Phys. Lett. 2001, 350, 522.
dc.identifier.citedreferenceE. Heyer, K. Benelhadj, S. Budzák, D. Jacquemin, J. Massue, G. Ulrich, Chem. - Eur. J. 2017, 23, 7324.
dc.identifier.citedreferenceS. Sarkar, H. P. Hendrickson, D. Lee, F. Devine, J. Jung, E. Geva, J. Kim, B. D. Dunietz, J. Phys. Chem. C 2017, 121, 3771.
dc.identifier.citedreferenceJ. Gibson, A. P. Monkman, T. J. Penfold, ChemPhysChem 2016, 2956.
dc.identifier.citedreferenceE. W. Evans, Y. Olivier, Y. Puttisong, W. K. Myers, T. J. H. Hele, S. M. Menke, T. H. Thomas, D. Credgington, D. Beljonne, R. H. Friend, N. C. Greenham, J. Phys. Chem. Lett. 2018, 9, 4053.
dc.identifier.citedreferenceJ. Gibson, T. J. Penfold, Phys. Chem. Chem. Phys. 2017, 19, 8428.
dc.identifier.citedreferenceI. Kim, S. O. Jeon, D. Jeong, H. Choi, W. J. Son, D. Kim, Y. M. Rhee, H. S. Lee, J. Chem. Theory Comput. 2020, 16, 621.
dc.identifier.citedreferenceM. K. Etherington, J. Gibson, H. F. Higginbotham, T. J. Penfold, A. P. Monkman, Nat. Commun. 2016, 7, 13680.
dc.identifier.citedreferenceT. Hosokai, H. Noda, H. Nakanotani, T. Nawata, Y. Nakayama, H. Matsuzaki, C. Adachi, J. Photonics Energy 2018, 8, 032102.
dc.identifier.citedreferenceM. Kasha, Discuss. Faraday Soc. 1950, 9, 14.
dc.identifier.citedreferenceY. Zhu, Y. Guan, Y. Niu, P. Wang, R. Chen, Y. Wang, P. Wang, H.-L. Xie, Adv. Opt. Mater. 2021, 9, 2100782.
dc.identifier.citedreferenceM. S. Kwon, Y. Yu, C. Coburn, A. W. Phillips, K. Chung, A. Shanker, J. Jung, G. Kim, K. Pipe, S. R. Forrest, J. H. Youk, J. Gierschner, J. Kim, Nat. Commun. 2015, 6.
dc.identifier.citedreferenceM. S. Kwon, D. Lee, S. Seo, J. Jung, J. Kim, Angew. Chem. 2014, 126, 11359.
dc.identifier.citedreferenceT. Ma, T. Li, L. Zhou, X. Ma, J. Yin, X. Jiang, Nat. Commun. 2020, 11, 1811.
dc.identifier.citedreferenceS. Zhao, H. Ma, M. Wang, C. Cao, J. Xiong, Y. Xu, S. Yao, Photochem. Photobiol. Sci. 2010, 9, 710.
dc.identifier.citedreferenceO. Bolton, K. Lee, H.-J. Kim, K. Y. Lin, J. Kim, Nat. Chem. 2011, 3, 205.
dc.identifier.citedreferenceZ. An, C. Zheng, Y. Tao, R. Chen, H. Shi, T. Chen, Z. Wang, H. Li, R. Deng, X. Liu, W. Huang, Nat. Mater. 2015, 14, 685.
dc.identifier.citedreferenceD. Lee, O. Bolton, B. C. Kim, J. H. Youk, S. Takayama, J. Kim, J. Am. Chem. Soc. 2013, 135, 6325.
dc.identifier.citedreferenceH. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature 2012, 492, 234.
dc.identifier.citedreferenceK. Benelhadj, W. Muzuzu, J. Massue, P. Retailleau, A. Charaf-Eddin, A. D. Laurent, D. Jacquemin, G. Ulrich, R. Ziessel, Chem. - Eur. J. 2014, 20, 12843.
dc.identifier.citedreferenceK.-C. Tang, M.-J. Chang, T.-Y. Lin, H.-A. Pan, T.-C. Fang, K.-Y. Chen, W.-Y. Hung, Y.-H. Hsu, P.-T. Chou, J. Am. Chem. Soc. 2011, 133, 17738.
dc.identifier.citedreferenceS. Haldar, D. Chakraborty, B. Roy, G. Banappanavar, K. Rinku, D. Mullangi, P. Hazra, D. Kabra, R. Vaidhyanathan, J. Am. Chem. Soc. 2018, 140, 13367.
dc.identifier.citedreferenceK. Wu, T. Zhang, Z. Wang, L. Wang, L. Zhan, S. Gong, C. Zhong, Z.-H. Lu, S. Zhang, C. Yang, J. Am. Chem. Soc. 2018, 140, 8877.
dc.identifier.citedreferenceM. Mamada, K. Inada, T. Komino, W. J. Poscavage Jr., H. Nakanotani, C. Adachi, ACS Cent. Sci. 2017, 3, 769.
dc.identifier.citedreferenceA. K. Gupta, W. Li, A. Ruseckas, C. Lian, C. L. Carpenter-Warren, D. B. Cordes, A. M. Z. Slawin, D. Jacquemin, I. D. W. Samuel, E. Zysman-Colman, ACS Appl. Mater. Interfaces 2021, 13, 15459.
dc.identifier.citedreferenceY. Long, M. Mamada, C. Li, P. L. dos Santos, M. Colella, A. Danos, C. Adachi, A. Monkman, J. Phys. Chem. Lett. 2020, 11, 3305.
dc.identifier.citedreferenceA. S. Berezin, K. A. Vinogradova, V. P. Krivopalov, E. B. Nikolaenkova, V. F. Plyusnin, A. S. Kupryakov, N. v. Pervukhina, D. Y. Naumov, M. B. Bushuev, Chem. – Eur. J. 2018, 24, 12790.
dc.identifier.citedreferenceY. Cao, J. Eng, T. J. Penfold, J. Phys. Chem. A 2019, 123, 2640.
dc.identifier.citedreferenceR. M. Khisamov, A. A. Ryadun, T. S. Sukhikh, S. N. Konchenko, Mol. Syst. Des. Eng. 2021, 6, 1056.
dc.identifier.citedreferenceF. Liang, L. Wang, D. Ma, X. Jing, F. Wang, Appl. Phys. Lett. 2002, 81, 4.
dc.identifier.citedreferenceD. Sahoo, T. Adhikary, P. Chowdhury, S. C. Roy, S. Chakravorti, Chem. Phys. 2008, 352, 175.
dc.working.doiNOen
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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