Paper
Organic & Biomolecular Chemistry
Notes and references
1 (a) K.-T. Wong, H.-F. Chen and F.-C. Fang, Org. Lett., 2006,
8, 3501; (b) K.-T. Wong, R.-T. Chen, F.-C. Fang, C.-C. Wu
and Y.-T. Lin, Org. Lett., 2005, 7, 1979; (c) P.-I. Shih,
C.-H. Chien, C.-Y. Chuang, C.-F. Shu, C.-H. Yang,
J.-H. Chen and Y. Chi, J. Mater. Chem., 2007, 17, 1692;
(d) S. Ye, Y. Liu, C. Di, H. Xi, W. Wu, Y. Wen, K. Lu, C. Du,
Y. Liu and G. Yu, Chem. Mater., 2009, 21, 1333;
(e) N. A. Sheddan and J. Mulzer, Org. Lett., 2005, 7, 5115.
2 (a) K.-T. Wong, T.-Y. Hwu, A. Balaiah, T.-C. Chao,
F.-C. Fang, C.-T. Lee and Y.-C. Peng, Org. Lett., 2006, 8,
1415; (b) C. Wu, T.-L. Liu, W.-Y. Hung, Y.-T. Lin,
K.-T. Wong, R.-T. Chen, Y.-M. Chen and Y.-Y. Chien, J. Am.
Chem. Soc., 2003, 125, 3710; (c) C. Ego, A. C. Grimsdale,
F. Uckert, G. Yu, G. Srdanov and K. Müllen, Adv. Mater.,
2002, 14, 809; (d) S.-Y. Qiu, H. Xu, L. Li, H.-T. Xu,
L.-K. Meng, H.-S. Pang, C. Tang, Z.-Q. Pang, J. Xiao,
X. Wang, S.-H. Ye, Q.-L. Fan and W. Huang, J. Phys. Chem.
C, 2017, 121, 9230.
3 (a) K.-T. Wong, Z.-J. Wang, Y.-Y. Chien and C.-L. Wang, Org.
Lett., 2001, 3, 2285; (b) S. L. Tao, Z. K. Peng, X. H. Zhang,
P. F. Wang, C.-S. Lee and S.-T. Lee, Adv. Funct. Mater., 2005,
15, 1716; (c) Z. H. Li, M. S. Wong, H. Fukutani and Y. Tao,
Org. Lett., 2006, 8, 4271; (d) J. A. Mikroyannidis, L. Fenenko
and C. Adachi, J. Phys. Chem. B, 2006, 110, 20317.
4 (a) M. Gasonoo, A. Sumita, K. N. Boblak, K. Giuffre,
T. Ohwada and D. A. Klumpp, J. Org. Chem., 2017, 82, 6044;
(b) Q. Dong, H. Lian, Z. Gao, Z. Guo, N. Xiang, Z. Zhong,
H. Guo, J. Huang and W. Y. Wong, Dyes Pigm., 2017, 137,
84; (c) M. F. Grünberg, F. Jia, A. R. Nass and L. J. Gooßen,
Adv. Synth. Catal., 2016, 358, 1589; (d) Z. Zhang, Z. Zhang,
D. Ding, Y. Wei, H. Xu, J. Jia, Y. Zhao, K. Pan and
W. Huang, J. Phys. Chem. C, 2014, 118, 20559; (e) B. Y. Ren,
C. J. Ou, C. Zhang, Y. Z. Chang, M. D. Yi, J. Q. Liu,
L. H. Xie, G. W. Zhang, X. Y. Deng, S. B. Li, W. Wei and
W. Huang, J. Phys. Chem. C, 2012, 116, 8881.
Fig. 2 UV and PL spectra of product 8 in CH2Cl2 solution.
standard (see the details in the ESI†). Besides, the thermal
property of product 8 was examined by differential scanning
calorimetry (DSC) and thermogravimetric analysis (TGA). The
glass transition temperature (Tg) of product 8 was found to be
100 °C while the decomposition temperature (Td) was up to
379 °C (Fig. S1†), which indicated excellent thermal and mor-
phological stability of 8.
In addition, the UV and PL spectra of pyrene and com-
pound 8 were also tested and compared, indicating the impor-
tance of conjugated structures between pyrene and fluorene
units (Fig. S2†).
Conclusions
In conclusion, a library of indole-containing 9,9-diarylfluor-
enes and other electron-rich (hetero)arene adducts were syn-
thesized in the presence of scandium triflate. This new strategy
exhibited high yield, mild reaction conditions and good sub-
strate compatibility. Preliminary exploration of the optical
property and morphological stability of some products and
new pyrenyl substituted 9,9-diarylfluorene with nonplanar con-
formations may likely foreshadow their further applications in
electroluminescent materials such as OLED.
5 K.-T. Wong, Y.-Y. Chien, R.-T. Chen, C. F. Wang, Y. T. Lin,
H.-H. Chiang, P.-Y. Hsieh, C.-C. Wu, C. H. Chou, Y. O. Su,
G.-H. Lee and S.-M. Peng, J. Am. Chem. Soc., 2002, 124,
11576.
6 P.-I. Shih, C.-L. Chiang, A. K. Dixit, C.-K. Chen, M. C. Yuan,
R.-Y. Lee, C.-T. Chen, E. W.-G. Diau and C.-F. Shu, Org.
Lett., 2006, 8, 2799.
7 Z. Peng, S. Tao, X. Zhang, J. Tang, C. S. Lee and S.-T. Lee,
J. Phys. Chem. C, 2008, 112, 2165.
Conflicts of interest
There are no conflicts to declare.
8 (a) W.-L. Yu, J. Pei, W. Huang and A. J. Heeger, Adv. Mater.,
2000, 12, 828; (b) D.-H. Hwang, M.-J. Park and J.-H. Lee,
Mater. Sci. Eng., C, 2004, 24, 201; (c) P.-I. Shih, C.-H. Chien,
F.-I. Wu and C.-F. Shu, Adv. Funct. Mater., 2007, 17, 3514;
(d) S. Ye, Y. Liu, K. Lu, W. Wu, C. Du, Y. Liu, H. Liu, T. Wu
and G. Yu, Adv. Funct. Mater., 2010, 20, 3125; (e) S. Ye,
Y. Liu, J. Chen, K. Lu, W. Wu, C. Du, Y. Liu, T. Wu, Z. Shuai
and G. Yu, Adv. Mater., 2010, 22, 4167.
Acknowledgements
This research was financially supported by the National Nature
Science Foundation of China (21772039, 21272069). We grate-
fully acknowledge the financial support from the Central
Universities and Key Laboratory of Organofluorine Chemistry,
Shanghai Institute of Organic Chemistry, Chinese Academy of
Sciences.
9 (a) H. T. Ang, J. P. G. Rygus and D. G. Hall, Org. Biomol.
Chem., 2019, 17, 6007; (b) Q. Wu, G.-L. Li, S. Yang,
9618 | Org. Biomol. Chem., 2019, 17, 9615–9619
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