Self-Assembled Helical Arrays for the Stabilization of the Triplet State.
carbazole
helicity
phenylmethanone
ultralong phosphorescence
waveguiding
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
27 Jul 2020
27 Jul 2020
Historique:
received:
08
04
2020
pubmed:
6
5
2020
medline:
6
5
2020
entrez:
6
5
2020
Statut:
ppublish
Résumé
Room-temperature phosphorescence of metal and heavy atom-free organic molecules has emerged as an area of great potential in recent years. A rational design played a critical role in controlling the molecular ordering to impart efficient intersystem crossing and stabilize the triplet state to achieve room-temperature ultralong phosphorescence. However, in most cases, the strategies to strengthen phosphorescence efficiency have resulted in a reduced lifetime, and the available nearly degenerate singlet-triplet energy levels impart a natural competition between delayed fluorescence and phosphorescence, with the former one having the advantage. Herein, an organic helical assembly supports the exhibition of an ultralong phosphorescence lifetime. In contrary to other molecules, 3,6-phenylmethanone functionalized 9-hexylcarbazole exhibits a remarkable improvement in phosphorescence lifetime (>4.1 s) and quantum yield (11 %) owing to an efficient molecular packing in the crystal state. A right-handed helical molecular array act as a trap and exhibits triplet exciton migration to support the exceptionally longer phosphorescence lifetime.
Identifiants
pubmed: 32367621
doi: 10.1002/anie.202005105
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
13079-13085Subventions
Organisme : Science and Engineering Research Board
ID : CRG/2019/002539
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
A. Forni, E. Lucenti, C. Botta, E. Cariati, J. Mater. Chem. C 2018, 6, 4603;
M. Baroncini, G. Bergamini, P. Ceroni, Chem. Commun. 2017, 53, 2081;
G. Baryshnikov, B. Minaev, H. Ågren, Chem. Rev. 2017, 117, 6500;
X. Yang, G. Zhou, W.-Y. Wong, Chem. Soc. Rev. 2015, 44, 8484.
Z. Yu, Y. Wu, L. Xiao, J. Chen, Q. Liao, J. Yao, H. Fu, J. Am. Chem. Soc. 2017, 139, 6376;
S. M. A. Fateminia, Z. Mao, S. Xu, Z. Yang, Z. Chi, B. Liu, Angew. Chem. Int. Ed. 2017, 56, 12160;
Angew. Chem. 2017, 129, 12328;
G. Zhang, G. M. Palmer, M. Dewhirst, C. L. Fraser, Nat. Mater. 2009, 8, 747.
V. C. Wakchaure, K. C. Ranjeesh, Goudappagouda, T. Das, K. Vanka, R. Gonnade, S. S. Babu, Chem. Commun. 2018, 54, 6028;
G. He, B. D. Wiltshire, P. Choi, A. Savin, S. Sun, A. Mohammadpour, M. J. Ferguson, R. McDonald, S. Farsinezhad, A. Brown, K. Shankar, E. Rivard, Chem. Commun. 2015, 51, 5444.
Goudappagouda, A. Manthanath, V. C. Wakchaure, K. C. Ranjeesh, T. Das, K. Vanka, T. Nakanishi, S. S. Babu, Angew. Chem. Int. Ed. 2019, 58, 2284;
Angew. Chem. 2019, 131, 2306;
O. M. S. Kwon, D. Lee, S. Seo, J. Jung, J. Kim, Angew. Chem. Int. Ed. 2014, 53, 11177;
Angew. Chem. 2014, 126, 11359;
O. Bolton, K. Lee, H. J. Kim, K. Y. Lin, J. Kim, Nat. Chem. 2011, 3, 205.
Kenry, C. Chen, B. Liu, Nat. Commun. 2019, 10, 2111;
S. Hirata, J. Mater. Chem. C 2018, 6, 11785;
S. Xu, R. Chen, C. Zheng, W. Huang, Adv. Mater. 2016, 28, 9920;
Y. Li, M. Gecevicius, J. Qiu, Chem. Soc. Rev. 2016, 45, 2090;
H. Chen, X. Ma, S. Wu, H. Tian, Angew. Chem. Int. Ed. 2014, 53, 14149;
Angew. Chem. 2014, 126, 14373;
S. K. Lower, M. A. El-Sayed, Chem. Rev. 1966, 66, 199.
S. Kuila, S. J. George, Angew. Chem. Int. Ed. 2020, https://doi.org/10.1002/anie.202002555;
Angew. Chem. 2020, https://doi.org/10.1002/ange.202002555;
S. Kuila, K. V. Rao, S. Garain, P. K. Samanta, S. Das, S. K. Pati, M. Eswaramoorthy, S. J. George, Angew. Chem. Int. Ed. 2018, 57, 17115;
Angew. Chem. 2018, 130, 17361.
R. Kabe, N. Notsuka, K. Yoshida, C. Adachi, Adv. Mater. 2016, 28, 655;
S. Hirata, K. Totani, J. Zhang, T. Yamashita, H. Kaji, S. R. Marder, T. Watanabe, C. Adachi, Adv. Opt. Mater. 2013, 1, 438;
C. S. Bilen, N. Harrison, D. J. Morantz, Nature 1978, 271, 235.
Y. Xiong, Z. Zhao, W. Zhao, H. Ma, Q. Peng, Z. He, X. Zhang, Y. Chen, X. He, J. W. Y. Lam, B. Z. Tang, Angew. Chem. Int. Ed. 2018, 57, 7997;
Angew. Chem. 2018, 130, 8129;
Z. He, W. Zhao, J. W. Y. Lam, Q. Peng, H. Ma, G. Liang, I. Shuai, B. Z. Tang, Nat. Commun. 2017, 8, 416;
W. Zhao, Z. He, J. W. Y. Lam, Q. Peng, H. Ma, Z. Shuai, G. Bai, J. Hao, B. Z. Tang, Chem 2016, 1, 592.
L. Gu, H. Shi, M. Gu, K. Ling, H. Ma, S. Cai, L. Song, C. Ma, H. Li, G. Xing, X. Hang, J. Li, Y. Gao, W. Tao, Z. Shuai, Z. An, X. Liu, W. Huang, Angew. Chem. Int. Ed. 2018, 57, 8425;
Angew. Chem. 2018, 130, 8561;
S. Cai, H. Shi, Z. Zhang, X. Wang, H. Ma, N. Gan, Q. Wu, Z. Cheng, K. Ling, M. Gu, C. Ma, L. Gu, Z. An, W. Huang, Angew. Chem. Int. Ed. 2018, 57, 4005;
Angew. Chem. 2018, 130, 4069;
Z. 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.
Z. He, H. Gao, S. Zhang, S. Zheng, Y. Wang, Z. Zhao, D. Ding, B. Yang, Y. Zhang, W. Z. Yuan, Adv. Mater. 2019, 31, 1807222;
T. Ogoshi, H. Tsuchida, T. Kakuta, T. Yamagishi, A. Taema, T. Ono, M. Sugimoto, M. Mizuno, Adv. Funct. Mater. 2018, 28, 1707369;
S. Hirata, M. Vacha, Adv. Opt. Mater. 2017, 5, 1600996;
Y. Xie, Y. Ge, Q. Peng, C. Li, Q. Li, Z. Li, Adv. Mater. 2017, 29, 1606829;
Z. Yang, Z. Mao, X. Zhang, D. Ou, Y. Mu, Y. Zhang, C. Zhao, S. Liu, Z. Chi, J. Xu, Y.-C. Wu, P.-Y. Lu, A. Lien, M. R. Bryce, Angew. Chem. Int. Ed. 2016, 55, 2181;
Angew. Chem. 2016, 128, 2221;
J. Wei, B. Liang, R. Duan, Z. Cheng, C. Li, T. Zhou, Y. Yi, Y. Wang, Angew. Chem. Int. Ed. 2016, 55, 15589;
Angew. Chem. 2016, 128, 15818;
Y. Katsurada, S. Hirata, K. Totani, M. Watanabe, M. Vacha, Adv. Opt. Mater. 2015, 3, 1726.
M. Li, K. Ling, H. Shi, N. Gan, L. Song, S. Cai, Z. Cheng, L. Gu, X. Wang, C. Ma, M. Gu, Q. Wu, L. Bian, M. Liu, Z. An, H. Ma, W. Huang, Adv. Opt. Mater. 2019, 7, 1800820;
B. Zhou, D. Yan, Adv. Funct. Mater. 2019, 29, 1807599;
L. Gu, H. Shi, L. Bian, M. Gu, K. Ling, X. Wang, H. Ma, S. Cai, W. Ning, L. Fu, H. Wang, S. Wang, Y. Gao, W. Yao, F. Huo, Y. Tao, Z. An, X. Liu, W. Huang, Nat. Photonics 2019, 13, 406;
L. Bian, H. Shi, X. Wang, K. Ling, H. Ma, M. Li, Z. Cheng, C. Ma, S. Cai, Q. Wu, N. Gan, X. Xu, Z. An, W. Huang, J. Am. Chem. Soc. 2018, 140, 10734;
Z. Chai, C. Wang, J. Wang, F. Liu, Y. Xie, Y.-Z. Zhang, J.-R. Li, Q. Lia, Z. Li, Chem. Sci. 2017, 8, 8336.
H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature 2012, 492, 234.
E. Yashima, N. Ousaka, D. Taura, K. Shimomura, T. Ikai, K. Maeda, Chem. Rev. 2016, 116, 13752;
C. C. Lee, C. Grenier, E. W. Meijer, A. P. H. J. Schenning, Chem. Soc. Rev. 2009, 38, 671;
A. Maity, M. Gangopadhyay, A. Basu, S. Aute, S. S. Babu, A. Das, J. Am. Chem. Soc. 2016, 138, 11113.
W. Li, Q. Huang, Z. Mao, Q. Li, L. Jiang, Z. Xie, R. Xu, Z. Yang, J. Zhao, T. Yu, Y. Zhang, M. P. Aldred, Z. Chi, Angew. Chem. Int. Ed. 2018, 57, 12727;
Angew. Chem. 2018, 130, 12909;
Z. Zhang, L. Tang, X. Fan, Y. Wang, K. Zhang, Q. Sun, H. Zhang, S. Xue, W. Yang, J. Mater. Chem. C 2018, 6, 8984.
N. J. Turro, Modern Molecular Photochemistry, University Science Books, Sausalito, 1978.
C. Chen, Z. Chi, K. C. Chong, A. S. Batsanov, Z. Yang, Z. Mao, Z. Yang, B. Liu, ChemRxiv 2019, https://doi.org/10.26434/chemrxiv.9895724.
G. Wang, B. Xiong, C. Zhou, Y. Liu, W. Xu, C.-A. Yang, K.-W. Tang, W.-Y. Wong, Chem. Asian J. 2019, 14, 4365;
H.-R. Bjørsvik, V. Elumalai, Eur. J. Org. Chem. 2016, 5474.
K. Nagarajan, A. R. Mallia, K. Muraleedharan, M. Hariharan, Chem. Sci. 2017, 8, 1776;
S. Hirata, M. Vacha, J. Phys. Chem. Lett. 2016, 7, 1539;
P. Ravat, T. Šolomek, M. Rickhaus, D. Häussinger, M. Neuburger, M. Baumgarten, M. Juríček, Angew. Chem. Int. Ed. 2016, 55, 1183;
Angew. Chem. 2016, 128, 1198;
M. Rickhaus, M. Mayor, M. Juríček, Chem. Soc. Rev. 2016, 45, 1542.
H. Liu, Z. Bian, Q. Cheng, L. Lan, Y. Wang, H. Zhang, Chem. Sci. 2019, 10, 227.
A. B. Vasista, H. Jog, T. Heilpern, M. E. Sykes, S. Tiwari, D. K. Sharma, S. K. Chaubey, G. P. Wiederrecht, S. K. Gray, G. V. P. Kumar, Nano Lett. 2018, 18, 650.
D. Chaudhuri, D. Li, Y. Che, E. Shafran, J. M. Gerton, L. Zang, J. M. Lupton, Nano Lett. 2011, 11, 488-492.
A. Köhler, H. Bässler, J. Mater. Chem. 2011, 21, 4003.