One-step synthesis of cyclic compounds towards easy room-temperature phosphorescence and deep blue thermally activated delayed fluorescence

Article abstract of DOI:10.1039/c8cc03833c

With the advantages of facile one-pot synthesis and THF-irrigating purification, we first developed novel cyclic compounds with deep blue thermally activated delayed fluorescence (TADF) and room-temperature phosphorescence (RTP) dual emission even in the

Full text of DOI:10.1039/c8cc03833c

View Article Online
View Journal
ChemComm
Accepted Manuscript
This article can be cited before page numbers have been issued, to do this please use: H. yingyuan, Z.
Wang, X. Jiang, X. Cai, S. Su, F. Huang and Y. Cao, Chem. Commun., 2018, DOI: 10.1039/C8CC03833C.
Volume 52 Number
1
4
January 2016 Pages 1–216
This is an Accepted Manuscript, which has been through the
Royal Society of Chemistry peer review process and has been
accepted for publication.
ChemComm
Chemical Communications
www.rsc.org/chemcomm
Accepted Manuscripts are published online shortly after
acceptance, before technical editing, formatting and proof reading.
Using this free service, authors can make their results available
to the community, in citable form, before we publish the edited
article. We will replace this Accepted Manuscript with the edited
and formatted Advance Article as soon as it is available.
You can find more information about Accepted Manuscripts in the
author guidelines.
Please note that technical editing may introduce minor changes
to the text and/or graphics, which may alter content. The journal’s
standard Terms & Conditions and the ethical guidelines, outlined
in our author and reviewer resource centre, still apply. In no
event shall the Royal Society of Chemistry be held responsible
for any errors or omissions in this Accepted Manuscript or any
consequences arising from the use of any information it contains.
ISSN 1359-7345
COMMUNICATION
Marilyn M. Olmstead, Alan L. Balch, Josep M. Poblet, Luis Echegoyenet al.
Reactivity differences of Sc
first methanofullerene derivatives of Sc
3
N@C2n (2n
=
68 and 80). Synthesis of the
3
N@D5h-C80
rsc.li/chemcomm

Page 1 of 5
ChemComm
View Article Online
DOI: 10.1039/C8CC03833C

ChemComm
Page 2 of 5
View Article Online
DOI: 10.1039/C8CC03833C

Page 3 of 5
ChemComm
View Article Online
DOI: 10.1039/C8CC03833C

Please d Co hn eomt Ca do jmu smt margins
Page 4 of 5
View Article Online
DOI: 10.1039/C8CC03833C
COMMUNICATION
Journal Name
promote new work to study unique fine optical properties of
cyclic compounds. In addition, simpler preparation process
realizing RTP could accelerate the pace of innovative
commercial applications and fluorescence/phosphorescence
dual-emission feature is useful such as in white-light lighting
and security marking applications.
2016, 55, 2181-2185; (n) S. Hirata, Adv. Optical Mater., 2017,
, 1700116.
(a) Q. Zhang, B. Li, S. Huang, H. Nomura, H. Tanaka and C.
Adachi, Nat. Photon., 2014, , 326-332; (b) Y. Tao, K. Yuan, T.
Chen, P. Xu, H. Li, R. Chen, C. Zheng, L. Zhang and W. Huang,
Adv. Mater., 2014, 26, 7931-7958; (c) X. Cai, B. Gao, X. L. Li, Y.
Cao and S. J. Su, Adv. Funct. Mater., 2016, 26, 8042-8052; (d)
T. Hatakeyama, K. Shiren, K. Nakajima, S. Nomura, S.
Nakatsuka, K. Kinoshita, J. Ni, Y. Ono and T. Ikuta, Adv. Mater.,
5
8
8
This work was financially supported by the National Key
R&D Program of China (2016YFB0401004), the National Natural
Science Foundation of China (51625301, 51573059 and
2
016, 28, 2777-2781; (e) J. C. Yong, K. J. Sang, S. S. Lee, E. Yu
and J. Y. Lee, Chem. Mater., 2016, 28, 5400-5405; (f) M. Y.
Wong and E. Zysman-Colman, Adv. Mater., 2017, 29, 1605444;
(g) Z. Yang, Z. Mao, Z. Xie, Y. Zhang, S. Liu, J. Zhao, J. Xu, Z. Chi
and M. P. Aldred, Chem. Soc. Rev., 2017, 46, 915-1016; (h) Y.
Liu, C. Li, Z. Ren, S. Yan and M. R. Bryce, Nat. Rev. Mater., 2018,
9
1233116), 973 Project (2015CB655003), and Guangdong
Provincial Department of Science and Technology
2016B090906003 and 2016TX03C175).
(
3
, 18020; (i) T. T. Bui, F. Goubard, M. Ibrahim-Ouali, D. Gigmes
and F. Dumur, Beilstein J. Org. Chem., 2018, 14, 282-308.
W. Li, D. Liu, F. Shen, D. Ma, Z. Wang, T. Feng, Y. Xu, B. Yang
and Y. Ma, Adv. Funct. Mater., 2012, 22, 2797-2803.
0 Z. He, X. Cai, Z. Wang, D. Chen, Y. Li, H. Zhao, K. Liu, Y. Cao, S.
J. Su, Sci. China Chem., 2018, 61, DOI: 10.1007/s11426-017-
Notes and references
9
1
1
(a) H. Sun, S. Liu, W. Lin, K. Y. Zhang, W. Lv, X. Huang, F. Huo,
H. Yang, G. Jenkins, Q. Zhao and W. Huang, Nat. Commun.,
2
014,
and T. Aida, Nat. Mater., 2005,
(a) G. Zhang, G. M. Palmer, M. W. Dewhirst and C. L. Fraser,
Nat. Mater., 2009, , 747-751 ; (b) L. Yuan, W. Lin, K. Zheng, L.
5
, 3601; (b) A. Kishimura, T. Yamashita, K. Yamaguchi
9
219-x
4
, 546-549.
1
1
1 H. Uoyama, K. Goushi, K. Shizu, H. Nomura and C. Adachi,
Nature, 2012, 492, 234-238.
2 (a) J. S. Ward, R. S. Nobuyasu, A. S. Batsanov, P. Data, A. P.
Monkman, F. B. Dias and M. R. Bryce, Chem. Commun., 2016,
52, 2612-2615; (b) R. Huang, J. Avó, T. Northey, E. Chaning-
2
3
8
He and W. Huang, Chem. Soc. Rev., 2013, 42, 622-661
(a) R. B. Thompson, Fluorescence Sensors & Biosensors, CRC,
Boca Raton, FL, 2005; (b) G. Zhang, J. Chen, S. J. Payne, S. E.
Kooi, J. N. Demas and C. L. Fraser, J. Am. Chem. Soc., 2007, 129
Pearce, P. L. D. Santos, J. S. Ward, P. Data, M. K. Etherington,
M. A. Fox, T. J. Penfold, M. N. Berberan-Santos, J. C. Lima, M.
,
8
2
942-8943; (c) W. Wu, R. Tang, Q. Li and Z. Li, Chem. Soc. Rev.,
015, 44, 3997-4022; (d) S. S. Lucky, K. C. Soo and Y. Zhang,
R. Bryce and F. B. Dias, J. Mater. Chem. C, 2017,
c) L. Yu, Z. Wu, C. Zhong, G. Xie, Z. Zhu, D. Ma and C. Yang,
Adv. Optical Mater., 2017, , 1700588.
3 (a) R. Kabe, N. Notsuka, K. Yoshida and C. Adachi, Adv. Mater.,
016, 28, 655-660; (b) N. Notsuka, R. Kabe, K. Goushi and C.
5, 6269-6280;
(
Chem. Rev., 2015, 115, 1990-2042.
(a) A. J. C. Kuehne and M. C. Gather, Chem. Rev., 2016, 116,
5
4
5
1
1
1
Hatakeyama and C. Adachi, Adv. Optical Mater., 2017,
2823-12864; (b) H. Nakanotani, T. Furukawa, T. Hosokai, T.
5,
700051; (c) H. Zhang, B. Tang, C. Wang and Y. Wang, Angew.
2
Adachi, Adv. Funct. Mater., 2017, 27, 1703902.
4 (a) S. Menning, M. Krämer, B. A. Coombs, F. Rominger, A.
1
Chem. Int. Ed., 2017, 56, 12543-12547.
Beeby, A. Dreuw and U. H. Bunz, J. Am. Chem. Soc., 2013, 135
2
,
(a) M. A. Baldo, D. F. O'Brien, Y. You, A. Shoustikov, S. Sibley,
M. E. Thompson and S. R. Forrest, Nature, 1998, 395, 151-154;
160-2163; (b) M. S. Kwon, D. Lee, S. Seo, J. Jung and J. Kim,
Angew. Chem. Int. Ed., 2014, 53, 11177-11181; (c) Z. Mao, Z.
Yang, Y. Mu, Y. Zhang, Y. F. Wang, Z. Chi, C. C. Lo, S. Liu, A. Lien
and J. Xu, Angew. Chem. Int. Ed., 2015, 54, 6270-6273; (d) Y.
Gong, L. Zhao, Q. Peng, D. Fan, W. Z. Yuan, Y. Zhang and B. Z.
(
2
2
b) Y. Ma, H. Zhang, J. Shen and C. Che, Synth. Met., 1998, 94,
45-248; (c) F. Templier, OLED Microdisplays, Wiley, Hoboken,
014.
6
7
(a) C. W. Tang and S. A. Vanslyke, Appl. Phys. Lett., 1987, 51
13-915; (b) B. K. An, D. S. Lee, J. S. Lee, Y. S. Park, H. S. Song
and S. Y. Park, J. Am. Chem. Soc., 2004, 126, 10232-10233.
(a) C. S. Bilen, N. Harrison and D. J. Morantz, Nature, 1978, 271
35-237; (b) O. Bolton, K. Lee, H. J. Kim, K. Y. Lin and J. Kim,
Nat. Chem., 2011, , 207-212; (c) S. Hirata, K. Totani, H. Kaji,
M. Vacha, T. Watanabe and C. Adachi, Adv. Optical Mater.,
013, , 438-442; (d) S. Hirata, K. Totani, J. Zhang, T.
,
Tang, Chem. Sci., 2015,
5 R. C. Evans, P. Douglas and C. J. Winscom, Coord. Chem. Rev.,
006, 250, 2093-2126.
6, 4438-4444.
9
1
1
2
,
6 (a) S. Y. Lee, T. Yasuda, H. Nomura and C. Adachi, Appl. Phys.
Lett., 2012, 101, 093306; (b) Q. Zhang, J. Li, K. Shizu, S. Huang,
S. Hirata, H. Miyazaki and C. Adachi, J. Am. Chem. Soc., 2012,
134, 14706-14709; (c) H. Tanaka, K. Shizu, H. Miyazaki and C.
Adachi, Chem. Commun., 2012, 48, 11392-11394.
7 J. A. Seo, Y. Im, S. H. Han, C. W. Lee and J. Y. Lee, ACS Appl.
Mater. Interfaces, 2017, 9, 37864-37872.
8 K. Matsui, S. Oda, K. Yoshiura, K. Nakajima, N. Yasuda and T.
Hatakeyama, J. Am. Chem. Soc., 2018, 140, 1195-1198.
9 A. Köhler and H. Bässler, Electronic Processes in Organic
Semiconductors, Wiley-VCH, Weinheim, 2015.
2
3
2
1
Yamashita, H. Kaji, S. R. Marder, T. Watanabe and C. Adachi,
Adv. Funct. Mater., 2013, 23, 3386-3397; (e) D. Lee, O. Bolton,
B. C. Kim, J. H. Youk, S. Takayama and J. Kim, J. Am. Chem. Soc.,
1
1
1
2
2
013, 135, 6325-6329; (f) S. Reineke, N. Seidler, S. R. Yost, F.
Prins, W. A. Tisdale and M. A. Baldo, Appl. Phys. Lett., 2013,
03, 093302; (g) Y. Gong, G. Chen, Q. Peng, W. Z. Yuan, Y. Xie,
S. Li, Y. Zhang and B. Z. Tang, Adv. Mater., 2015, 27, 6195-6201;
h) S. K. Min, Y. Yu, C. Coburn, A. W. Phillips, K. Chung, A.
Shanker, J. Jung, G. Kim, K. Pipe and S. R. Forrest, Nat.
Commun., 2015, , 8947; (i) P. Xue, J. Sun, P. Chen, P. Wang,
B. Yao, P. Gong, Z. Zhang and R. Lu, Chem. Commun., 2015, 51
0381-10384 ; (j) Z. An, C. Zheng, Y. Tao, R. Chen, H. Shi, T.
Chen, Z. Wang, H. Li, R. Deng, X. Liu and W. Huang, Nat. Mater.,
015, 14, 685-690; (k) X. Chen, C. Xu, T. Wang, C. Zhou, J. Du,
Z. Wang, H. Xu, T. Xie, G. Bi and J. Jiang, Angew. Chem. Int. Ed.,
016, 55, 9872-9876; (l) J. Wei, B. Liang, R. Duan, Z. Cheng, C.
Li, T. Zhou, Y. Yi and Y. Wang, Angew. Chem. Int. Ed., 2016, 55
5589-15593; (m) Z. Yang, Z. Mao, X. Zhang, D. Ou, Y. Mu, Y.
1
0 (a) U. J. Lorenz and T. R. Rizzo, J. Am. Chem. Soc., 2014, 136
4974-14980; (b) D. Beljonne, Z. Shuai, G. Pourtois and J. L.
Bredas, J. Phys. Chem. A, 2001, 105, 3899-3907.
,
(
1
6
,
1
2
2
,
1
Zhang, C. Zhao, S. Liu, Z. Chi, J. Xu, et al, Angew. Chem. Int. Ed.,
4
| J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Page 5 of 5
ChemComm
View Article Online
DOI: 10.1039/C8CC03833C
One-step synthesis of cyclic compounds towards easy room-temperature
phosphorescence and deep blue thermally activated delayed fluorescence
Yingyuan Hu,† Zhenfeng Wang,† Xiaofang Jiang, Xinyi Cai, Shi-Jian Su,* Fei Huang*
and Yong Cao
Novel cyclic compounds were first synthesized by facile one-pot synthesis and
THF-irrigating purification, interestingly, which simultaneously exhibited deep blue
thermally activated delayed fluorescence and room-temperature phosphorescence
dual emission even under the condition of as-spun neat film.