10.1002/ejoc.201701741
European Journal of Organic Chemistry
COMMUNICATION
[15] Y. Li, G. Zhang, W. Zhang, J.Wang, X. Chen, Z. Liu, Y.
Yan, Y. Zhao, D. Zhang; Chem. Asian. J. 2014, 9, 3207-
3214.
[16] S.L. Suraru, F. Würthner, Synthesis. 2009, 11, 1841-1845.
[17] S. Chopin, F. Chaignon, E. Blart, F. Odobel, J. Mater.
Chem. 2007, 17, 4139–4146.
[18] F. Doria, M. Nadai, G. Costa, G. Sattin, C. Gallati, G.
Bergamaschi, F. Moraca, S. Alcaro, M. Freccero, S.N.
Richter, Eur. J. Org. Chem. 2016, 28, 4824–4833.
[19] F. Doria, C.M. Gallati, M. Freccero, Org. Biomol. Chem.,
2013, 11, 7838–7842.
shift of EL is seen compare 1a substituted NDI and
unsubstituted N,N’-dihexyl-NDI.[36]
.
In summary, acetylene substituted naphthalene diimides
were synthesized via an efficient and straightforward approach.
The electroluminescence ability of such types of compounds
was demonstrated for the first time. The compounds bearing
aldehyde (1c) and trimethylsilyl (1b) units can be considered as
substrates for further synthesis of molecules with a core
consisting of acetylene substituted naphthalene diimides for
organic electronics devices. Further modifications of these
compounds are in progress.
[20] W. Fan, Ch. Liu, Y. Li, Z. Wanga. Chem. Commun. 2017,
53, 188-191.
[21] Y. Li, G. Zhang, Z. Liu, X. Chen, J. Wang, Ch. Di, D.
Zhang, Macromolecules. 2013, 46, 5504−5511.
[22] F. Chaignon, M. Falkenstro, S. Karlsson, E. Blart, F.
Odobel, L. Hammarstrom, Chem. Commun. 2007, 1, 64–
66.
[23] Q. Li, M. Peng, H. Li, Ch. Zhong, L. Zhang, X. Cheng, X.
Peng, Q. Wang, J. Qin, Z. Li, Org. Lett., 14, 2012, 2094–
2097.
Acknowledgements
The calculations have been carried out in Wroclaw Centre for
grant no. 18. Thanks to K. Bednarczyk for making TGA
measurements.
Keywords:
core-substituted
naphthalene
diimides
•
[24] H.S. Mehr, N.C.Romano, R. Altamimi, J.M. Modarellic, D.A.
Modarelli, Dalton Trans. 2015, 44, 3176–3184.
photoluminescence • elcetrochemistry • electroluminescence
[25] F. Doria, M. Antonio, M. Benotti, D.Verga, M. Freccero,
J.Org.Chem., 2009, 74, 8616–8625
[26] M. Korzec, P. Bartczak, A. Niemczyk, J. Szade, M.
[1] M.A. Kobaisi, S.V. Bhosale, K. Latham, A.M. Raynor,
Sheshanath Chem. Rev. 2016, 116, 11685-11796.
[2] H. Sasabe, J. Kido, Eur. J. Org. Chem. 2013, 7653–7663
[3] M.E. Ragoussi, M. Ince, T. Torres, Eur. J. Org. Chem.
2013, 6475–6489.
[4] Y. Ooyama, Y. Harima, Eur. J. Org. Chem. 2009, 2903–
2934.
[5] A. Operamolla, G.M. Farinola, Eur. J. Org. Chem. 2011,
423–450.
Kapkowski, P. Zenderowska, K. Balin, J. Lelatko, J.
Polanski, Journal of Catalysis. 2014, 313, 1-8.
[27] M. Rams-Baron, M. Dulski, A. Mrozek-Wilczkiewicz, M.
Korzec, W. Cieslik, E. Spaczyńska, P. Bartczak, A.
Ratuszna, J. Polanski, R. Musiol, Plos One. 2015, 1-17.
[28] R. Chinchilla, C. Najera, Chem. Soc. Rev. 2011, 40, 5084–
5121.
[6] N. Sakai, J. Mareda, E. Wautheyb, S. Matile, Chem.
Commun. 2010, 46, 4225-4237.
[7] L.M. Kozycz, Ch. Guo, J.G. Manion, A.J. Tilley, A.J. Lough,
Y. Li, D.S. Seferos, J. Mater. Chem. C. 2015, 3, 11505-
11515.
[29] M. Karak, L.C.A. Barbosa, G.C. Hargadenc, RSC Adv., 2014,
4, 53442–53466.
[30] B. Wang, Y. Wang, X. Guo, Z. Jiao, G. Jin, X. Guo,
Catalysis Communications, 2017, 101, 36–39
[31] A.M.Thomas, A. Sujatha; G. Anilkumar, RSC Adv. 2014, 4,
21688–21698.
[8] T. Zhang, M. Lu, W. Wang, W. Lv, Cui, J. Feng, W.; Ling,
Q. Dyes and Pigments 2017, 146, 169-177.
[32] P. Zhang, Y. Zhou, M. Fan, P. Jiang, Chinese Journal of
Catalysis, 2015, 36, 2036–2043.
[33] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria,
[9] Ch. Zhan, J. Yao, Chem. Mater. 2016, 28, 1948−1964.
[10] A. Pron, P. Gawrys, M. Zagorska, D. Djurado, R. Demadrille,
Chem. Soc. Rev., 2010, 39, 2577–2632.
[11] A.A. Berezin, A. Sciutto, N. Demitri, D. Bonifazi, Org. Lett.
2015, 17, 870−1873.
[12] X. Guo, W.G. Mark, Org. Lett. 2008, 10, 5333-5336.
[13] Y. Li, M. Baghernejad, A.G. Qusiy, D.Z. Manrique, G.
Zhang, J. Hamill, Y. Fu, P. Broekmann, W. Hong, T.
Wandlowski, D. Zhang, C. Lambert, Angew. Chem. Int. Ed.
2015, 54, 13586 –13589.
M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B.
Mennucci, G.A. Petersson, et al. Gaussian, Inc., Gaussian
09, Revision A.1, Wallingford CT, 2009.
[34] N.M. O'Boyle, A.L. Tenderholt, K.M. Langner, J. Comp.
Chem. 2008, 29, 839-845.
[35] P. Wiederrecht, B. A. Yoon, M. R. Wasielewski, Adv.
Mater., 1996, 8, 535
[36] Y. Ofir, A. Zelichenok, S. Yitzchaik, J. Mater. Chem., 2006,
16, 2142–2149
[14] Y. Li, G. Zhang, G. Yang, Y. Guo, Ch. Di, X. Chen, Z. Liu,
H. Liu, Z. Xu, W. Xu, H. Fu, D. Zhang, J. Org. Chem. 2013,
78, 926−2934.
This article is protected by copyright. All rights reserved.