Communication
ChemComm
˜
˜
14 R. Nu´nez, I. Romero, F. Teixidor and C. Vinas, Chem. Soc. Rev., 2016,
45, 5147.
decay for the ICT transition involving the o-carborane moiety.
Furthermore, these results imply that linking planar aryl rings to
o-carborane cages can turn on the ICT-based radiative decay
mechanism.
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15 J. Cabrera-Gonzalez, V. Sanchez-Arderiu, C. Vinas, T. Parella,
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F. Teixidor and R. Nu´nez, Inorg. Chem., 2016, 55, 11630.
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16 R. Nu´nez, M. Tarres, A. Ferrer-Ugalde and F. Fabrizi de Biani, Chem.
Rev., 2016, 116, 14307.
In conclusion, we prepared and characterised distorted and
planar terphenyl-based o-carboranyl compounds (TCB and FCB).
The solid-state structure of TCB showed perfectly distorted terphenyl
rings. Although TCB exhibited LE-based emission in THF at
298 K, under the same conditions, FCB demonstrated intense
emission that was attributable to ICT transitions involving the
o-carborane cage. Interestingly, increasing the planarity of the
terphenyl group enhanced the quantum efficiency and radiative
decay efficiency. Consequently, these results definitively indicate
that the planarity of the aryl groups appended on o-carborane is
critical for controlling the ICT-based radiative decay of o-carborane
substituted compounds.
This work was supported by the Basic Science Research Program
(2017R1D1A1B03035412 for D. K. An and 2018R1D1A1B07040387
for K. M. Lee), the Basic Research Laboratory Program
(2017R1A4A1015405 for K. M. Lee), and the Nano Material
Technology Development Program (NRF2016M3A7B4909246
for K. M. Lee) through the National Research Foundation of
Korea (NRF) funded by the Ministry of Science and ICT.
17 S. Mukherjee and P. Thilagar, Chem. Commun., 2016, 52, 1070.
18 K. O. Kirlikovali, J. C. Axtell, A. Gonzalez, A. C. Phung, S. I. Khan and
A. M. Spokoyny, Chem. Sci., 2016, 7, 5132.
19 Y. Kim, S. Park, Y. H. Lee, J. Jung, S. Yoo and M. H. Lee, Inorg. Chem.,
2016, 55, 909.
20 D. Tu, P. Leong, S. Guo, H. Yan, C. Lu and Q. Zhao, Angew. Chem.,
Int. Ed., 2017, 56, 11370.
21 N. Shin, S. Yu, J. H. Lee, H. Hwang and K. M. Lee, Organometallics,
2017, 36, 1522.
22 I. Nar, A. Atsay, A. Altındal and E. Hamuryudan, Inorg. Chem., 2018,
57, 2199.
23 H. Jin, H. J. Bae, S. Kim, J. H. Lee, H. Hwang, M. H. Park and
K. M. Lee, Dalton Trans., 2019, 48, 1467.
24 J. O. Huh, H. Kim, K. M. Lee, Y. S. Lee, Y. Do and M. H. Lee, Chem.
Commun., 2010, 46, 1138.
25 K. M. Lee, J. O. Huh, T. Kim, Y. Do and M. H. Lee, Dalton Trans.,
2011, 40, 11758.
26 C. A. Lugo, C. E. Moore, A. L. Rheingold and V. Lavallo, Inorg. Chem.,
2015, 54, 2094.
27 K. Kokado and Y. Chujo, J. Org. Chem., 2011, 76, 316.
28 B. P. Dash, R. Satapathy, E. R. Gaillard, K. M. Norton, J. A. Maguire,
N. Chug and N. S. Hosmane, Inorg. Chem., 2011, 50, 5485.
29 K.-R. Wee, W.-S. Han, D. W. Cho, S. Kwon, C. Pac and S. O. Kang,
Angew. Chem., Int. Ed., 2012, 51, 2677.
30 S. Kwon, K.-R. Wee, Y.-J. Cho and S. O. Kang, Chem. – Eur. J., 2014,
20, 5953.
31 H. Naito, Y. Morisaki and Y. Chujo, Angew. Chem., Int. Ed., 2015,
54, 5084.
Conflicts of interest
¨
32 L. Weber, J. Kahlert, R. Brockhinke, L. Bohling, A. Brockhinke, H.-G.
Stammler, B. Neumann, R. A. Harder and M. A. Fox, Chem. – Eur. J.,
2012, 18, 8347.
There are no conflicts to declare.
33 K.-R. Wee, Y.-J. Cho, J. K. Song and S. O. Kang, Angew. Chem., Int. Ed.,
2013, 52, 9682.
Notes and references
´
˜
´
34 A. Ferrer-Ugalde, A. Gonzalez-Campo, C. Vinas, J. Rodrıguez-Romero,
´
¨¨
˜
1 V. I. Bregadze, Chem. Rev., 1992, 92, 209.
R. Santillan, N. Farfan, R. Sillanpaa, A. Sousa-Pedrares, R. Nu´nez and
´
´
´
˜
˜
2 A. Gonzalez-Campo, E. J. Juarez-Perez, C. Vinas, B. Boury,
¨¨
F. Teixidor, Chem. – Eur. J., 2014, 20, 9940.
¨
R. Sillanpaa, R. Kivekas and R. Nu´nez, Macromolecules, 2008, 35 H. Naito, K. Nishino, Y. Morisaki, K. Tanaka and Y. Chujo, Angew.
41, 8458. Chem., Int. Ed., 2017, 56, 254.
3 R. N. Grimes, Carboranes, Academic Press, London, 2nd edn, 2011. 36 X. Wu, J. Guo, Y. Cao, J. Zhao, W. Jia, Y. Chen and D. Jia, Chem. Sci.,
4 F. Issa, M. Kassiou and L. M. Rendina, Chem. Rev., 2011, 111, 5701. 2018, 9, 5270.
5 K.-R. Wee, Y.-J. Cho, S. Jeong, S. Kwon, J.-D. Lee, I.-H. Suh and 37 J. Li, C. Yang, X. Peng, Y. Chen, Q. Qi, X. Luo, W.-Y. Lai and
S. O. Kang, J. Am. Chem. Soc., 2012, 134, 17982. W. Huang, J. Mater. Chem. C, 2018, 6, 19.
6 A. Ferrer-Ugalde, E. J. Juarez-Perez, F. Teixidor, C. Vinas and 38 K. Nishino, H. Yamamoto, K. Tanaka and Y. Chujo, Org. Lett., 2016,
´
´
˜
˜
R. Nu´nez, Chem. – Eur. J., 2013, 19, 17021.
18, 4064.
7 T. Kim, H. Kim, K. M. Lee, Y. S. Lee and M. H. Lee, Inorg. Chem., 39 A. V. Marsh, N. J. Cheetham, M. Little, M. Dyson, A. J. P. White,
2013, 52, 160.
8 A. M. Spokoyny, Pure Appl. Chem., 2013, 85, 903.
P. Beavis, C. N. Warriner, A. C. Swain, P. N. Stavrinou and
M. Heeney, Angew. Chem., Int. Ed., 2018, 57, 10640.
`
˜
9 J. Poater, M. Sola, C. Vinas and F. Teixidor, Angew. Chem., Int. Ed., 40 K. Nishino, K. Uemura, K. Tanaka, Y. Morisaki and Y. Chujo, Eur.
2014, 53, 1191. J. Org. Chem., 2018, 1507.
10 H. J. Bae, J. Chung, H. Kim, J. Park, K. M. Lee, T.-W. Koh, Y. S. Lee, 41 J. H. Lee, H. Hwang and K. M. Lee, J. Organomet. Chem., 2016,
S. Yoo, Y. Do and M. H. Lee, Inorg. Chem., 2014, 53, 128. 825, 69.
11 Y. H. Lee, J. Park, J. Lee, S. U. Lee and M. H. Lee, J. Am. Chem. Soc., 42 M. F. Hawthorne, T. E. Berry and P. A. Wegner, J. Am. Chem. Soc.,
2015, 137, 8018. 1965, 87, 4746.
12 Y. H. Lee, J. Park, S.-J. Jo, M. Kim, J. Lee, S. U. Lee and M. H. Lee, 43 T. E. Paxson, K. P. Callahan and M. F. Hawthorne, Inorg. Chem.,
Chem. – Eur. J., 2015, 21, 2052. 1973, 12, 708.
13 J. Poater, M. Sola, C. Vinas and F. Teixidor, Chem. – Eur. J., 2016, 44 W. Jiang, C. B. Knobler and M. F. Hawthorne, Inorg. Chem., 1996,
`
˜
22, 7437.
35, 3056.
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Chem. Commun., 2019, 55, 14518--14521 | 14521