Journal of the American Chemical Society
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21, 1149; (e) Li, Y.; Liu, Y.; Zhou, H.; Chen, W.; Mei, J.; Su, J. Chem.—
Eur. J. 2017, 23, 9280.
the award of a Science and Engineering Research Fellowship.
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5
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A.P.M. acknowledges the EPSRC for funding under grant num-
ber EP/L02621X/1. P.R.M. acknowledges the support of an
EPSRC First Grant (EP/N029992/1) and a Royal Society Re-
search Grant (RG150558). The authors thank Dr Lars-Olof
Pålsson, Dr Qing He, Prof David Parker, and Prof Andy Beeby
for access to instruments and useful discussions.
13. (a) Kido, J.; Shionoya, H.; Nagai, K. Appl. Phys. Lett. 1995, 67,
2281; (b) Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.;
Kwok, H. S.; Zhan, X.; Liu, Y.; Zhuc, D.; Tang, B. Z. Chem. Commun.
2001, 1740; (c) Gao, X.-C.; Cao, H.; Huang, L.; Huang, Y.-Y.; Zhang,
B.-W.; Huang, C.-H. Appl. Surf. Sci. 2003, 210, 183; (d) Chen, J.; Xu,
B.; Ouyang, X.; Tang, B. Z.; Cao, Y. J. Phys. Chem. A 2004, 108, 7522;
(e) Zhao, Y. S.; Peng, A.; Fu, H.; Ma, Y.; Yao, J. Adv. Mater. 2008, 20,
1661; (f) Shimizu, M.; Tatsumi, H.; Mochida, K.; Shimono, K.;
Hiyama, T. Chem.—Asian J. 2009, 4, 1289; (g) Zhang, Z. Y.; Xu, B.;
Su, J. H.; Shen, L. P.; Xie, Y. S.; Tian, H. Angew. Chem. Int. Ed. 2011,
50, 11654; (h) Feng, J.; Chen, X.; Han, Q.; Wang, H.; Lu, P.; Wang, Y.
J. Lumin. 2011, 131, 2775; (i) Yang, L.; Ye, J.; Xu, L.; Yang, X.; Gong,
W.; Lin, Y.; Ning, G. RSC Adv. 2012, 2, 11529; (j) Zhang, X.; Ye, J.;
Xu, L.; Yang, L.; Deng, D.; Ning, G. J. Lumin. 2013, 139, 28; (k) Zhao,
Z.; He, B.; Nie, H.; Chen, B.; Lu, P.; Qin, A.; Tang, B. Z. Chem. Com-
mun. 2014, 50, 1131; (l) Kojima, T.; Hiraoka, S. Org. Lett. 2014, 16,
1024; (m) Wunderlich, K.; Larsen, A.; Marakis, J.; Fytas, G.; Klap-
per, M.; Müllen, K. Small 2014, 10, 1914; (n) Zhang, J.; Xu, B.; Chen,
J.; Ma, S.; Dong, Y.; Wang, L.; Li, B.; Ye, L.; Tian, W. Adv. Mater.
2014, 26, 739; (o) Chang, Z. F.; Jing, L. M.; Wei, C.; Dong, Y. P.; Ye,
Y. C.; Zhao, Y. S.; Wang, J. L. Chem.—Eur. J. 2015, 21, 8504; (p) Zhu,
Q.; Zhang, Y.; Nie, H.; Zhao, Z.; Liu, S.; Wong, K. S.; Tang, B. Z. Chem.
Sci. 2015, 6, 4690; (q) Lungerich, D.; Reger, D.; Hçlzel, H.; Riedel,
R.; Martin, M. M. J. C.; Hampel, F.; Jux, N. Angew. Chem. Int. Ed.
2016, 55, 5602; (r) Vij, V.; Bhalla, V.; Kumar, M. Chem. Rev. 2016,
116, 9565; (s) Zhang, Y.; He, B.; Luo, W.; Peng, H.; Chen, S.; Hu, R.;
Qin, A.; Zhao, Z.; Tang, B. Z. J. Mater. Chem. C 2016, 4, 9316; (t)
Yang, J.; Ren, Z.; Xie, Z.; Liu, Y.; Wang, C.; Xie, Y.; Peng, Q.; Xu, B.;
Tian, W.; Zhang, F.; Chi, Z.; Li, Q.; Li, Z. Angew. Chem. Int. Ed. 2017,
56, 880.
14. We use the term 'dimer' to describe the pairs of similar (but
not chemically equivalent) phenyl rings that exhibit close, face-to-
face aromatic interactions through either an intra- or intermolec-
ular contacts. To avoid confusion, we have chosen not to use
terms such as 'excimer', which normally describes an intermolec-
ular dimer formed in the excited state, and other more specific
terminology.
15. Emission spectra are reported in eV and are Jacobian correct-
ed to allow meaningful comparisons of Stokes shifts between
compounds, see: Mooney, J.; Kambhampati, P. J. Phys. Chem. Lett.
2013, 4, 3316.
16. Previous reports have shown that the increasing viscosities of
cold 2-MeTHF solutions can lead to restriction of molecular rota-
tion, see: Lewis, F. D.; Liu, W. Z. J. Phys. Chem. A 2002, 106, 1976.
17. Durig, J. R.; Kizer, K. L.; Karriker, J. M., J. Raman Spectrosc.
1973, 1, 17.
18. Glass transition temperatures (Tg) have been determined
previously for 2-MeTHF and 1:5 v/v MCH–i-pentane, see: (a)
Kliger, D. S. Ultrasensitive Laser Spectroscopy. 1st ed.; Academic
Press: New York, 1983; (b) Mizukami, M.; Fujimori, H.; Oguni, M.
Prog. Theor. Phys. Suppl. 1997, 79.
REFERENCES
1. (a) Zhao, Y. S.; Fu, H.; Hu, F.; Peng, A. D.; Yao, J. Adv. Mater. 2007,
19, 3554; (b) Xiao, Y.; Peng, H. D.; Wang, J. Y.; Wu, H. D.; Liu, Z. H.;
Pan, G. B. Phys. Chem. Chem. Phys. 2016, 18, 7019.
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
2. (a) Shin, W. S.; Lee, M.-G.; Verwilst, P.; Lee, J. H.; Chi, S.-G.; Kim, J.
S. Chem. Sci. 2016, 7, 6050; (b) Nicol, A.; Qin, W.; Kwok, R. T. K.;
Burkhartsmeyer, J. M.; Zhu, Z.; Su, H.; Luo, W.; Lam, J. W. Y.; Qian,
J.; Wong, K. S.; Tang, B. Z. Chem. Sci. 2017, 8, 4634; (c) Cheng, Y.;
Sun, C.; Ou, X.; Liu, B.; Lou, X.; Xia, F. Chem. Sci. 2017, 8, 4571.
3. (a) Yu, T.; Ou, D.; Yang, Z.; Huang, Q.; Mao, Z.; Chen, J.; Zhang, Y.;
Liu, S.; Xu, J.; Bryce, M. R.; Chi, Z. Chem. Sci. 2017, 8, 1163; (b) Oka-
zaki, M.; Takeda, Y.; Data, P.; Pander, P.; Higginbotham, H.; Monk-
man, A. P.; Minakata, S. Chem. Sci. 2017, 8, 2677; (c) Qi, Q. K.; Liu,
Y. F.; Fang, X. F.; Zhang, Y. M.; Chen, P.; Wang, Y.; Yang, B.; Xu, B.;
Tian, W. J.; Zhang, S. X. A. RSC Adv. 2013, 3, 7996; (d) Luo, X. L.;
Zhao, W. J.; Shi, J. Q.; Li, C. H.; Liu, Z. P.; Bo, Z. S.; Dong, Y. Q.; Tang,
B. Z. J. Phys. Chem. C 2012, 116, 21967.
4. (a) Zhao, Z.; Chen, S.; Lam, J. W. Y.; Wang, Z.; Lu, P.; Mahtab, F.;
Sung, H. H. Y.; Williams, I. D.; Ma, Y.; Kwok, H. S.; Tang, B. Z. J. Ma-
ter. Chem. 2011, 21, 7210; (b) Tsujimoto, H.; Ha, D. G.; Markopou-
los, G.; Chae, H. S.; Baldo, M. A.; Swager, T. M. J. Am. Chem. Soc.
2017, 139, 4894; (c) Tang, C. W.; Vanslyke, S. A. Appl. Phys. Lett.
1987, 51, 913.
5. (a) Xie, Z.; Yang, B.; Li, F.; Cheng, G.; Liu, L.; Yang, G.; Xu, H.; Ye,
L.; Hanif, M.; Liu, S.; Ma, D.; Ma, Y. J. Am. Chem. Soc. 2005, 127,
14152; (b) Lee, K. H.; Kwon, Y. S.; Lee, J. Y.; Kang, S.; Yook, K. S.;
Jeon, S. O.; Lee, J. Y.; Yoon, S. S. Chem.—Eur. J. 2011, 17, 12994; (c)
Mazumdar, P.; Das, D.; Sahoo, G. P.; Salgado-Moran, G.; Misra, A.
Phys. Chem. Chem. Phys. 2014, 16, 6283; (d) Sharma, K.; Kaur, S.;
Bhalla, V.; Kumar, M.; Gupta, A. J. Mater. Chem. A 2014, 2, 8369; (e)
Li, J.; Li, P.; Wu, J.; Gao, J.; Xiong, W. W.; Zhang, G.; Zhao, Y.; Zhang,
Q. J. Org. Chem. 2014, 79, 4438.
6. Wang, C.; Liu, Z.; Li, M.; Xie, Y.; Li, B.; Wang, S.; Xue, S.; Peng, Q.;
Chen, B.; Zhao, Z.; Li, Q.; Ge, Z.; Li, Z. Chem. Sci. 2017, 8, 3750.
7. (a) Kuimova, M. K.; Botchway, S. W.; Parker, A. W.; Balaz, M.;
Collins, H. A.; Anderson, H. L.; Suhling, K.; Ogilby, P. R. Nature
Chem. 2009, 1, 69; (b) Liu, T.; Liu, X.; Spring, D. R.; Qian, X.; Cui, J.;
Xu, Z. Sci. Rep. 2014, 4, 5418; (c) Vyšniauskas, A.; Qurashi, M.;
Gallop, N.; Balaz, M.; Anderson, H. L.; Kuimova, M. K. Chem. Sci.
2015, 6, 5773; (d) Sherin, P. S.; López-Duarte, I.; Dent, M. R.; Ku-
bánková, M.; Vyšniauskas, A.; Bull, J. A.; Reshetnikova, E. S.; Klym-
chenko, A. S.; Tsentalovich, Y. P.; Kuimova, M. K. Chem. Sci. 2017,
8, 3523; (e) Qian, H.; Cousins, M. E.; Horak, E. H.; Wakefield, A.;
Liptak, M. D.; Aprahamian, I. Nature Chem. 2017, 9, 83; (f)
Vyšniauskas, A.; Ding, D.; Qurashi, M.; Boczarow, I.; Balaz, M.; An-
derson, H. L.; Kuimova, M. K. Chem.—Eur. J. 2017, 23, 11001.
8. Qian, J.; Tang, B. Z. Chem 2017, 3, 56.
19. (a) Mendelovici, E.; Frost, R. L.; Kloprogge, T. J. Raman Spec-
trosc. 2000, 31, 1121; (b) Matsuura, H.; Miyazawa, T.; Hiraishi, M.
Spectrochim. Acta Part A Mol. Spectrosc. 1972, A 28, 2299.
20. The average expected intermolecular distances at these con-
centrations is approximately 100 nm. Variable concentration
studies show a lack of concentration-dependent shifts in emission
that would be expected for an intermolecular phenomenon. See
Figure S32.
21. Kuimova, M. K.; Yahioglu, G.; Levitt, J. A.; Suhling, K., J. Am.
Chem. Soc. 2008, 130, 6672.
22. Wiggins, P.; Williams, J. A.; Tozer, D. J. J. Chem. Phys. 2009, 131,
091101.
9. (a) Mei, J.; Hong, Y.; Lam, J. W.; Qin, A.; Tang, Y.; Tang, B. Z. Adv.
Mater. 2014, 26, 5429; (b) Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J.
W.; Tang, B. Z. Chem. Rev. 2015, 115, 11718; (c) Xiong, J. B.; Feng,
H. T.; Sun, J. P.; Xie, W. Z.; Yang, D.; Liu, M.; Zheng, Y. S. J. Am. Chem.
Soc. 2016, 138, 11469.
10. Ng, J. C. Y.; Liu, J.; Su, H.; Hong, Y.; Li, H.; Lam, J. W. Y.; Wong, K.
S.; Tang, B. Z. J. Mater. Chem. C 2014, 2, 78.
11. Lakowicz, J. R. Principles of Fluorescence Spectroscopy. 3rd ed.;
Springer: New York, 2006.
12. (a) Dong, Y.; Lam, J. W. Y.; Qin, A.; Liu, J.; Li, Z.; Tang, B. Z.; Sun,
J.; Kwok, H. S. Appl. Phys. Lett. 2007, 91, 011111; (b) Zhao, Z.; Lam,
J. W. Y.; Tang, B. Z. Curr. Org. Chem. 2010, 14, 2109; (c) Zhao, Z.;
Lam, J. W. Y.; Tang, B. Z. J. Mater. Chem. 2012, 22, 23726; (d) Qi, Q.;
Qian, J.; Ma, S.; Xu, B.; Zhang, S. X.; Tian, W. Chem.—Eur. J. 2015,
23. It is well known that the wavelengths of light emitted from
traditional, planar organic chromophores are dependent on the
overlap and orientation of π-surfaces. Although this analysis is
usually applied to large, polycyclic π-systems, such as perylene, it
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