Enhanced thermal stability and electro-optic activity from fluorene-based nonlinear optical chromophores

被引:7
作者
Liu, Fenggang [1 ]
Yu, Canwen [1 ]
Qin, Gangzhi [1 ]
Peng, Meishan [1 ]
Wang, Ziwei [1 ]
Li, Ziheng [1 ]
Wu, Shuangke [1 ]
Li, Chunlin [1 ]
Zhang, Maolin [2 ]
机构
[1] Guangzhou Univ, Sch Chem & Chem Engn, Guangzhou 510006, Peoples R China
[2] King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr KCC, Thuwal 239556900, Saudi Arabia
基金
中国国家自然科学基金;
关键词
Nonlinear optics; Chromophore; Isolation group; Electro-optic; Fluorene; FUNCTION-RELATIONSHIP EXPLORATION; SPHERICAL STRUCTURE; DESIGN; BRIDGE; COEFFICIENTS; PERFORMANCE; DENDRIMERS; POLYMERS; STATE;
D O I
10.1016/j.dyepig.2020.108751
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Two series of nonlinear optical chromophores G1-G4 and J1-J4 based on diethylaminophenyl or julolidinyl-based donor and tricyanovinyldihydrofuran acceptor have been synthesized. Compared to the unmodified isophorone bridge of chromophore G1 and J1, the bridges of chromophores G2/J2 and G3-G4/J3-J4 were modified with tert-butyldimethylsilyl (TBDMS) groups and fluorene group, respectively. In addition, we introduced bulky tert-butyldiphenylsilyl (TBDPS) groups to the donor of chromophore G4 and J4 to further increase poling efficiency. The results show that the chromophores G3-G4/J3-J4 modified with fluorene groups on the bridge have higher stability and larger electro-optic coefficient than chromophores G1-G2 and J1-J2. Electro-optical films doped with chromophore G1-G4 and J1-J4 have been poled to give r33 values of 69, 96, 118, 133, 143, 201, 240 and 261 pm/V at 1.31 mu m, respectively. All these provide valuable insight into understanding of the impact of an isolation group on the performance of chromophores.
引用
收藏
页数:8
相关论文
共 48 条
[11]   Novel nonlinear optical chromophores based on coumarin: Synthesis and properties studies [J].
Deng, Guowei ;
Xu, Huajun ;
Kuang, Lu ;
He, Chengcheng ;
Li, Bingke ;
Yang, Min ;
Zhang, Xiaoling ;
Li, Zhonghui ;
Liu, Jialei .
OPTICAL MATERIALS, 2019, 88 :218-222
[12]   Matrix-Assisted Poling of Monolithic Bridge-Disubstituted Organic NLO Chromophores [J].
Elder, Delwin L. ;
Benight, Stephanie J. ;
Song, Jinsheng ;
Robinson, Bruce H. ;
Dalton, Larry R. .
CHEMISTRY OF MATERIALS, 2014, 26 (02) :872-874
[13]  
Frisch M. J., 2019, Gaussian 16 Revision C.02
[14]   Linear and Third-Order Nonlinear Optical Properties of Chalcogenopyrylium-Terminated Heptamethine Dyes with Rigid, Bulky Substituents [J].
Getmanenko, Yulia A. ;
Allen, Taylor G. ;
Kim, Hyeongeu ;
Hales, Joel M. ;
Sandhu, Bhupinder ;
Fonari, Marina S. ;
Suponitsky, Kyrill Yu. ;
Zhang, Yadong ;
Khrustalev, Victor N. ;
Matichak, Jonathan D. ;
Timofeeva, Tatiana V. ;
Barlow, Stephen ;
Chi, San-Hui ;
Perry, Joseph W. ;
Marder, Seth R. .
ADVANCED FUNCTIONAL MATERIALS, 2018, 28 (46)
[15]   Site-isolated electro-optic chromophores based on substituted 2,2′-bis(3,4-propylenedioxythiophene) π-conjugated bridges [J].
Hammond, Scott R. ;
Clot, Olivier ;
Firestone, Kimberly A. ;
Bale, Denise H. ;
Lao, David ;
Haller, Marnie ;
Phelan, Gregory D. ;
Carlson, Brenden ;
Jen, Alex K. -Y. ;
Reid, Philip J. ;
Dalton, Larry R. .
CHEMISTRY OF MATERIALS, 2008, 20 (10) :3425-3434
[16]   Synthesis of chromophores with extremely high electro-optic activities. 2. Isophorone- and combined isophorone-thiophene-based chromophores [J].
He, MQ ;
Leslie, TM ;
Sinicropi, JA ;
Garner, SM ;
Reed, LD .
CHEMISTRY OF MATERIALS, 2002, 14 (11) :4669-4675
[17]   Synthesis of chromophores with extremely high electro-optic activity. 1. Thiophene-bridge-based chromophores [J].
He, MQ ;
Leslie, TM ;
Sinicropi, JA .
CHEMISTRY OF MATERIALS, 2002, 14 (11) :4662-4668
[18]   Novel nonlinear optical push-pull fluorene dyes chromophore as promising materials for telecommunications [J].
Huo, Fuyang ;
Zhang, Hua ;
Chen, Zhuo ;
Qiu, Ling ;
Liu, Jialei ;
Bo, Shuhui ;
Kityk, I. V. .
JOURNAL OF MATERIALS SCIENCE-MATERIALS IN ELECTRONICS, 2019, 30 (13) :12180-12185
[19]   Structure-function relationship exploration for enhanced thermal stability and electro-optic activity in monolithic organic NLO chromophores [J].
Jin, Wenwei ;
Johnston, Peter V. ;
Elder, Delwin L. ;
Manner, Karl T. ;
Garrett, Kerry E. ;
Kaminsky, Werner ;
Xu, Ruimin ;
Robinson, Bruce H. ;
Dalton, Larry R. .
JOURNAL OF MATERIALS CHEMISTRY C, 2016, 4 (15) :3119-3124
[20]   Ultralarge hyperpolarizability twisted π-electron system electro-optic chromophores:: Synthesis, solid-state and solution-phase structural characteristics, electronic structures, linear and nonlinear optical properties, and computational studies [J].
Kang, Hu ;
Facchetti, Antonio ;
Jiang, Hua ;
Cariati, Elena ;
Righetto, Stefania ;
Ugo, Renato ;
Zuccaccia, Cristiano ;
Macchioni, Alceo ;
Stern, Charlotte L. ;
Liu, Zhifu ;
Ho, Seng-Tiong ;
Brown, Eric C. ;
Ratner, Mark A. ;
Marks, Tobin J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3267-3286