Abstract
Organic second nonlinear optical chromophore GL-COOHs with two carboxyl groups are designed and synthesized in this paper. The structure of chromophore GL-COOHs are characterized by mass spectrum and nuclear magnetic resonance spectroscopy. The first order hyperpolarizability is studied by theoretical calculation, which is similar to the famous FTC chromophore. Thanks to the double carboxyl group structure, novel side chain polyester electro optic polymers are prepared based on chromophore GL-COOHs. Their Tgs are around 110 °C, which is high enough for keeping the long term stability of their electro optic activities. Their Tds are above 239 °C, which is high enough for the devices preparing process. Else, the largest d33 values are about 29.3, 43.6 and 63.1 pm/V for polymer GL-S-1, GL-S-2 and GL-S-3 respectively. Interestingly, there is a linear relation between chromophore loading density and d33 values.
Similar content being viewed by others
References
A. Hershko, A. Ciechanover, Annu. Rev. Biochem. 67, 425–479 (1998)
J. Liu, G. Xu, F. Liu, I. Kityk, X. Liu, Z. Zhen, RSC Adv. 5(21), 15784–15794 (2015)
C. Ouyang, J. Liu, Q. Liu, Y. Li, D. Yan, Q. Wang, M. Guo, A. Cao, ACS Appl. Mater. Interfaces 9(12), 10366–10370 (2017)
Y. Lin, X. Zhan, Acc. Chem. Res. 49(2), 175–183 (2016)
Y. Lin, Y. Li, X. Zhan, Chem. Soc. Rev. 41(11), 4245–4272 (2012)
J. Tour, Acc. Chem. Res. 33(11), 791–804 (2000)
K. Hirose, Y. Liang, Y. Kurosaka, A. Watanabe, T. Sugiyama, S. Noda, Nat. Photonics 25(1), 17–26 (2013)
Z. Shi, S. Hau, J.-D. Luo, T.-D. Kim, N.M. Tucker, J.-W. Ka, H. Sun, A. Pyajt, L. Dalton, Chen,A. Antao, A.K.-Y. Jen, Adv. Funct. Mater. 17, 2557 (2007)
J. Liu, P. Si, X. Liu, Z. Zhen, Opt. Mater. 47, 256 (2015)
O. Ostroverkhova, Chem. Rev. 116(22), 13279–13412 (2016)
S.H. Jang, J.D. Luo, N.M. Tucker, A. Leclercq, E. Zojer, M.A. Haller, T.D. Kim, J.W. Kang, K. Firestone, D. Bale, D. Lao, J.B. Benedict, D. Cohen, W. Kaminsky, B. Kahr, J.L. Bredas, P. Reid, L.R. Dalton, A.K.Y. Jen, Chem. Mater. 18, 2982 (2006)
J. Liu, W. Gao, I. Kityk, X. Liu, Zhen, Dyes Pigm. 122, 74–84 (2015)
F. Bures, H. Cermakova, J. Kulhanek, M. Ludwig, W. Kuznik, I. Kityk, T. Mikysek, A. Ruzicka, Eur. J. Org. Chem. 2012, 529 (2012)
F. Castet, V. Rodriguez, J. Pozzo, L. Ducasse, A. Plaquet, B. Champagne, Acc. Chem. Res. 46(11), 2656–2665 (2013)
J. Liu, W. Gao, X. Liu, Z. Zhen, Mater. Lett. 143, 333–335 (2015)
W. Wu, J. Qin, Z. Li, Polymer 54(17), 4354–4382 (2013)
Y. Li, T. Liu, H. Liu, M. Tian, Y. Li, Acc. Chem. Res. 47(4), 1186–1198 (2014)
K. Diemoz, J. Hein, S. Wilson, J. Fettinger, A. Franz, J. Org. Chem. 82(13), 6738–6747 (2017)
J. Liu, W. Hou, S. Feng, L. Qiu, X. Liu, Z. Zhen,, J. Phys. Org. Chem. 24, 439 (2011)
Y. Yang, F. Liu, H. Wang, M. Zhang, H. Xu, S. Bo, J. Liu, L. Qiu, Z. Zhen, X. Liu, Phys. Chem. Chem. Phys. 16(37), 20209–20215 (2014)
T. Zhang, H. Han, Y. Zou, Y. Lee, H. Oshima, K. Wong, R. Holmes, ACS Appl. Mater. Interfaces 9(30), 25418–25425 (2017)
P. Chen, Z. Li, Chin. J. Polym. Sci. 35(7), 793–798 (2017)
M. Zhang, G. Qin, J. Liu, Z. Zhen, A. Fedorchuk, G. Lakshminarayana, A. Albassam, A. Ei-Naggar, K. Ozga, I. Kityk, Chem. Phys. Lett. 681, 105–109 (2017)
Y. Li, T. Pullerits, M. Zhao, M. Sun, J. Phys. Chem. C 115(44), 21865–21873 (2011)
P. Song, Y. Li, F. Ma, T. Pullerits, M. Sun, J. Phys. Chem. C 117(31), 15879–15889 (2013)
Y. Li, B. Xu, P. Song, F. Ma, M. Sun, J. Phys. Chem. C 121(23), 12546–12561 (2017)
P. Song, Q. Zhou, Y. Li, F. Ma, M. Sun, Phys. Chem. Chem. Phys. 19, 16105–16112 (2017)
P. Song, Y. Li, F. Ma, T. Pullerits, M. Sun, Chem. Rec. 16, 734–753 (2016)
Y. Li, Y. Feng, M. Sun, Sci. Rep. 5, 13970 (2015)
P. Song, Y. Li, F. Ma, M. Sun, J. Mater. Chem. C, 3, 4810–4819 (2015)
G. Palma, M. Falconi, F. Starecki, V. Nazabal, J. Ari, L. Bodiou, J. Charrier, Y. Dumeige, E. Baudet, F. Prudenzano, Opt. Express 25, 7014–7030 (2017)
F. Tal, C. Dimas, J. Hu, A. Agarwal, L. Kinerling, Opt. Express 19, 11951–11962 (2011)
S. Kaloyanova, Y. Zagranyarski, S. Ritz, M. Hanulova, K. Koynov et al., J. Am. Chem. Soc. 138, 2881 (2016)
E. Kozma, G. Grisci, W. Mroz, M. Catellani, A. Eckstein-Andicsova et al., Dyes Pigm. 125, 201 (2016)
J. Zhou, X. Li, M. Wang, Mater. Lett. 172, 15 (2016)
J. Zhou, H. Yang, X. Li, M. Wang, J. Mater. Sci. Mater. Electron. 27, 2189–2194 (2016)
Z. Li, Q. Li, J. Qin, Polym. Chem. 2(12), 2723–2740 (2011)
F. Liu, M. Zhang, H. Xiao, Y. Yang, H. Wang, J. Liu, S. Bo, Z. Zhen, X. Liu, L. Qiu, J. Mater. Chem. C 3(36), 9283–9291 (2015)
C. Hu, F. Liu, H. Zhang, F. Huo, Y. Yang, H. Wang, H. Xiao, Z. Chen, J. Liu, L. Qiu, Z. Zhen, X. Liu, S. Bo, J. Mater. Chem. C 3(44), 11595–11604 (2015)
D. Li, B. Swanson, J. Robinson, M. Hoffbauer, J. Am. Chem. Soc. 115, 6975 (1993)
K. Bravaya, B. Grigorenko, A. Nemukhin, A. Krylov, Acc. Chem. Res. 45, 265 (2012)
H. Manzano, I. Esnal, T. Marques-Matesanz, J. Banuelos, I. Lopez-Arbeloa et al., Adv. Funct. Mater. 26, 2756 (2016)
L. He, X. Yang, Y. Liu, X. Kong, W. Lin, Chem. Commun. 52, 4029 (2016)
V. Padalkar, S. Seki, Chem. Soc. Rev. 45, 169 (2016)
M. He, T.M. Leslie, J.A. Sinicropi, Chem. Mater. 14, 2393 (2002)
C. Zhang, C. Lu, J. Zhu, G. Lu, X. Wang, Z. Shi, F. Liu, Y. Cui, Chem. Mater. 18, 6091–6093 (2006)
Gaussian 09, Revision C.01, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. MontgomeryJr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. .Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT, 2009
W. Koch, M. Holthausen, A Chemist’s Guide to Density Functional Theory (Wiley-VCH, Weinheim, 2000)
A. Becke, Phys. Rev. A 38, 3098–3100 (1988)
C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785–789 (1988)
C. Teng, H. Man, Appl. Phys. Lett. 56, 1734 (1990)
M. Mortazavi, A. Knoesen, S. Kowel, J. Opt. Soc. Am. B, 6, 733–741 (1989)
Acknowledgements
We are grateful to the Youth Foundation of Qinghai University (YFQHU.2013-0113) for financial support. And thanks for prof. Li in University of Electronic Science and technology for measurement of the EO polymers’ second harmonic generation.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Guo, L., Guo, Z. & Li, X. Design and preparation of side chain electro-optic polymeric materials based on novel organic second order nonlinear optical chromophores with double carboxyl groups. J Mater Sci: Mater Electron 29, 2577–2584 (2018). https://doi.org/10.1007/s10854-017-8181-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10854-017-8181-y