Modulation of Amplified Spontaneous Emissions between Singlet Fluorescence and Triplet Phosphorescence Channels in Organic Dye Lasers
Shuai Li
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorCorresponding Author
Zhenyi Yu
Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072 P. R. China
E-mail: [email protected]; [email protected]Search for more papers by this authorXiaoxiao Xiao
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorHua Geng
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorKai Wang
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorXue Jin
Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072 P. R. China
Search for more papers by this authorQing Liao
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorYi Liao
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorYishi Wu
Beijing National Laboratory for Molecular Sciences, Institute of chemistry, Chinese Academy of Sciences, Beijing, 100190 P. R. China
Search for more papers by this authorJiannian Yao
Beijing National Laboratory for Molecular Sciences, Institute of chemistry, Chinese Academy of Sciences, Beijing, 100190 P. R. China
Search for more papers by this authorCorresponding Author
Hongbing Fu
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072 P. R. China
E-mail: [email protected]; [email protected]Search for more papers by this authorShuai Li
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorCorresponding Author
Zhenyi Yu
Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072 P. R. China
E-mail: [email protected]; [email protected]Search for more papers by this authorXiaoxiao Xiao
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorHua Geng
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorKai Wang
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorXue Jin
Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072 P. R. China
Search for more papers by this authorQing Liao
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorYi Liao
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Search for more papers by this authorYishi Wu
Beijing National Laboratory for Molecular Sciences, Institute of chemistry, Chinese Academy of Sciences, Beijing, 100190 P. R. China
Search for more papers by this authorJiannian Yao
Beijing National Laboratory for Molecular Sciences, Institute of chemistry, Chinese Academy of Sciences, Beijing, 100190 P. R. China
Search for more papers by this authorCorresponding Author
Hongbing Fu
Beijing Key Laboratory for Optical Materials and Photonic Devices, Department of Chemistry, Beijing Advanced Innovation Center for Imaging Technology, Capital Normal University, Beijing, 100048 P. R. China
Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072 P. R. China
E-mail: [email protected]; [email protected]Search for more papers by this authorAbstract
Organic gain materials (OGMs) currently used in dye lasers and organic thin-film amplifiers are limited to singlet-fluorescence molecules. Although heavy-metal-containing phosphorescent emitters enable highly efficient organic light-emitting diodes, phosphorescent OGMs capable of light amplification by stimulated emission from triplet states remain largely unexplored. Demonstrated herein is the first phosphorescent dye laser from a pure organic luminescent rotor (1), composed of electron-donating sulfide-substituted difluoroboron (SBF2) and electron-accepting nitrobenzene (NB) moieties. Furthermore, modulation of amplified spontaneous emissions (ASEs) between singlet fluorescence and triplet phosphorescence channels is achieved by adjusting the relative rotation (dihedral angle θ) of the donor and acceptor moieties. Theoretical calculations and experimental results clarify that free and restricted rotor rotation regulates the T2 state below and above the S1 state, thus switching on and off the intersystem crossing from S1 to the high-lying T2 for phosphorescence and fluorescence, respectively. Based on this strategy, methyl groups are added on the NB moiety to increase the steric hindrance in 2, leading to tunable phosphorescence and/or fluorescence ASE. The results extend the scope of organic dye lasers and provide a strategy to develop phosphorescence OGMs capable of amplifying light through ASE from the triplet state.
Conflict of Interest
The authors declare no conflict of interest.
Supporting Information
Filename | Description |
---|---|
lpor201900036-sup-0001-suppMat.pdf2.9 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1A. J. Kuehne, M. C. Gather, Chem. Rev. 2016, 116, 12823.
- 2a) S. Chenais, S. Forget, Polym. Int. 2012, 61, 390; b) C. Zhang, Y. Yan, Y. S. Zhao, J. Yao, Acc. Chem. Res. 2014, 47, 3448.
- 3H. H. Fang, J. Yang, J. Feng, T. Yamao, S. Hotta, H. B. Sun, Laser Photonics Rev. 2014, 8, 687.
- 4C. Grivas, M. Pollnau, Laser Photonics Rev. 2012, 6, 419.
- 5L. Cerdan, J. Braborec, I. Garcia-Moreno, A. Costela, M. G. S. Londesborough, Nat. Commun. 2015, 6, 5958.
- 6I. D. W. Samuel, G. A. Turnbull, Chem. Rev. 2007, 107, 1272.
- 7F. P. Schafer, W. Schmidt, J. Volze, Appl. Phys. Lett. 1966, 9, 306.
- 8a) Z. Yu, W. Li, J. A. Hagen, Y. Zhou, D. Klotzkin, J. G. Grote, A. J. Steckl, Appl. Opt. 2007, 46, 1507; b) B. H. Wallikewitz, G. O. Nikiforov, H. Sirringhaus, R. H. Friend, Appl. Phys. Lett., 2012, 100, 173301; c) X. Liu, P. Stefanou, B. Wang, T. Woggon, T. Mappes, U. Lemmer, Opt. Express 2013, 21, 28941; d) K. Baumann, T. Stoeferle, N. Moll, G. Raino, R. F. Mahrt, T. Wahlbrink, J. Bolten, U. Scherf, J. Opt. 2010, 12, 065003.
- 9a) A. Mikosch, S. Ciftci, A. J. C. Kuehne, ACS Nano 2016, 10, 10195; b) H. Yamada, T. Nakamura, Y. Yamada, K. Yano, Adv. Mater. 2009, 21, 4134; c) N. Tetreault, A. Mihi, H. Miguez, I. Rodriguez, G. A. Ozin, F. Meseguer, V. Kitaev, Adv. Mater. 2004, 16, 346; d) M. Deutsch, Y. A. Vlasov, D. J. Norris, Adv. Mater. 2000, 12, 1176.
- 10a) S. Yuyama, T. Nakajima, K. Yamashita, K. Oe, Appl. Phys. Lett. 2008, 93, 023306; b) M. C. Gather, F. Ventsch, K. Meerholz, Adv. Mater. 2008, 20, 1966.
- 11a) W. Zhang, J. Yao, Y. S. Zhao, Acc. Chem. Res. 2016, 49, 1691; b) J. Clark, G. Lanzani, Nat. Photonics 2010, 4, 438; c) A. U. Khan, M. Kasha, Proc. Natl. Acad. Sci. U. S. A. 1983, 80, 1767.
- 12N. C. Giebink, S. R. Forrest, Phys. Rev. B 2009, 79.
- 13K. Goushi, K. Yoshida, K. Sato, C. Adachi, Nat. Photonics 2012, 6, 253.
- 14D. Di, A. S. Romanov, L. Yang, J. M. Richter, J. P. H. Rivett, S. Jones, T. H. Thomas, M. A. Jalebi, R. H. Friend, M. Linnolahti, M. Bochmann, D. Credgington, Science 2017, 356, 159.
- 15a) C. Adachi, M. A. Baldo, M. E. Thompson, S. R. Forrest, J. Appl. Phys. 2001, 90, 5048; b) D. Xia, B. Wang, B. Chen, S. Wang, B. Zhang, J. Ding, L. Wang, X. Jing, F. Wang, Angew. Chem., Int. Ed. 2014, 53, 1048.
- 16a) M. A. Baldo, R. J. Holmes, S. R. Forrest, Phys. Rev. B 2002, 66, 035321; b) T. Rabe, P. Gorrn, M. Lehnhardt, M. Tilgner, T. Riedl, W. Kowalsky, Phys. Rev. Lett. 2009, 102, 137401.
- 17M. Reufer, M. J. Walter, P. G. Lagoudakis, B. Hummel, J. S. Kolb, H. G. Roskos, U. Scherf, J. M. Lupton, Nat. Mater. 2005, 4, 340.
- 18O. G. Peterson, J. P. Webb, W. C. McColgin, J. H. Eberly, J. Appl. Phys. 1971, 42, 1917.
- 19a) O. Bolton, K. Lee, H. J. Kim, K. Y. Lin, J. Kim, Nat. Chem. 2011, 3, 205; b) L. Xiao, Y. Wu, J. Chen, Z. Yu, Y. Liu, J. Yao, H. Fu, J. Phys. Chem. A 2017, 121, 8652.
- 20Z. 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.
- 21a) Y. Gong, L. Zhao, Q. Peng, D. Fan, W. Z. Yuan, Y. Zhang, B. Z. Tang, Chem. Sci. 2015, 6, 4438; b) A. K. M. Shimizu, H. Sakaguchi, Eur. J. Org. Chem. 2016, 2016, 467; c) Z. He, W. Zhao, J. W. Y. Lam, Q. Peng, H. Ma, G. Liang, Z. Shuai, B. Z. Tang, Nat. Commun. 2017, 8, 416.
- 22D. Lee, O. Bolton, B. C. Kim, J. H. Youk, S. Takayama, J. Kim, J. Am. Chem. Soc. 2013, 135, 6325.
- 23Z. Yu, Y. Wu, L. Xiao, J. Chen, Q. Liao, J. Yao, H. Fu, J. Am. Chem. Soc. 2017, 139, 6376.
- 24a) Y. Yu, M. S. Kwon, J. Jung, Y. Zeng, M. Kim, K. Chung, J. Gierschner, J. H. Youk, S. M. Borisov, J. Kim, Angew. Chem., Int. Ed. 2017, 56, 16207; b) J. Xu, A. Takai, Y. Kobayashi, M. Takeuchi, Chem. Commun. 2013, 49, 8447.
- 25a) D.-H. Kim, A. D'Aleo, X.-K. Chen, A. D. S. Sandanayaka, D. Yao, L. Zhao, T. Komino, E. Zaborova, G. Canard, Y. Tsuchiya, E. Choi, J. W. Wu, F. Fages, J.-L. Bredas, J.-C. Ribierre, C. Adachi, Nat. Photonics 2018, 12, 98; b) H. Ye, D. H. Kim, X. Chen, A. S. D. Sandanayaka, J. U. Kim, E. Zaborova, G. Canard, Y. Tsuchiya, E. Y. Choi, J. W. Wu, F. Fages, J.-L. Bredas, A. D'Aleo, J.-C. Ribierre, C. Adachi, Chem. Mater. 2018, 30, 6702.
- 26M. A. Haidekker, T. P. Brady, D. Lichlyter, E. A. Theodorakis, Bioorg. Chem. 2005, 33, 415.
- 27a) W. Li, D. Liu, F. Shen, D. Ma, Z. Wang, T. Feng, Y. Xu, B. Yang, Y. Ma, Adv. Funct. Mater. 2012, 22, 2797; b) T. Ueno, Y. Urano, H. Kojima, T. Nagano, J. Am. Chem. Soc. 2006, 128, 10640.
- 28a) Z. Shuai, Q. Peng, Phys. Rep. 2014, 537, 123; b) Z. Shuai, Q. Peng, Natl. Sci. Rev. 2017, 4, 224.
- 29G. Baryshnikov, B. Minaev, H. Agren, Chem. Rev. 2017, 117, 6500.
- 30a) M. A. El-Sayed, Acc. Chem. Res. 1968, 1, 8; b) S. K. Lower, M. A. El-Sayed, Chem. Rev. 1966, 66, 199.
- 31M. Li, Q. Gao, P. Liu, Q. Liao, H. Zhang, J. Yao, W. Hu, Y. Wu, H. Fu, Adv. Funct. Mater. 2018, 28, 1707006.
- 32H. Ye, L. Cui, T. Matsushima, C. Qin, C. Adachi, ACS Appl. Mater. Interfaces 2018, 10, 27.
- 33X. Wang, Q. Liao, X. Lu, H. Li, Z. Xu, H. Fu, Sci. Rep. 2015, 4, 7011.