Structure-function relationship exploration for enhanced electro-optic activity in isophorone-based organic NLO chromophores

被引:39
作者
Liu, Fenggang [1 ]
Zhang, Hua [2 ]
Xiao, Hongyan [2 ]
Xu, Huajun [2 ]
Bo, Shuhui [2 ]
Qiu, Ling [2 ]
Zhen, Zhen [2 ]
Lai, Lijie [1 ]
Chen, Shujie [1 ]
Wang, Jiahai [1 ]
机构
[1] Guangzhou Univ, Guangzhou Key Lab Environm Funct Mat & Technol, Sch Chem & Chem Engn, Guangzhou 510006, Guangdong, Peoples R China
[2] Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
Nonlinear optics; Chromophore; Isolation group; Electro-optic; Isophorone; Structure-function; NONLINEAR-OPTICAL CHROMOPHORES; THERMAL-STABILITY; THIN-FILMS; DONOR; HYPERPOLARIZABILITY; OPTIMIZATION; DESIGN; SERIES;
D O I
10.1016/j.dyepig.2018.04.036
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Four isophorone-based chromophores FLD1-FLD4 has been synthesized and investigated based on julolidinyl donors, with modified isophorone-derived bridges and tricyanovinyl-dihydrofuran or phenyl-trifluoromethyltricyanofuran acceptors. The chromophore FLD3 was modified with a 2-((tert-butyldimethylsilyl)oxy)ethanethiol group covalently attached to the pi-conjugate bridge to ensure its all-trans conformation and prevent close packing of molecules, which benefit the macroscopic electro-optic efficiency. The chromophore FLD3 possesses better thermal stability than chromophore FLD1 without the isolation group on the bridge. Moreover, density functional theory calculations suggested that the hyperpolarizability (beta) value of chromophore FLD3 is larger than that of chromophore FLD1. Polymers doped with chromophore FLD3 have been poled to afford ultrahigh electro-optic coefficient (r(33)) of 238 pm/V at 1.31 pm, which is nearly 60% higher than that obtained from chromophore FLD1 and three times higher than that of analogue chromophores FLD2 and FLD4.
引用
收藏
页码:55 / 63
页数:9
相关论文
共 46 条
[1]  
[Anonymous], J EXP BIOL
[2]  
[Anonymous], CHEM MAT
[3]   Theory-guided enhancement of poling efficiency of organic electro-optic materials [J].
Benight, Stephanie J. ;
Johnson, Lewis E. ;
Knorr, Daniel B. ;
Bale, Denise H. ;
Kosilkin, Ilya ;
Olbricht, Benjamin C. ;
Sullivan, Philip A. ;
Reid, Philip J. ;
Robinson, Bruce H. ;
Overney, Rene M. ;
Jen, Alex K. -Y. ;
Steier, William H. ;
Kim, Seong-Ku ;
Fetterman, Harold ;
Prather, Dennis W. ;
Dalton, Larry R. .
LINEAR AND NONLINEAR OPTICS OF ORGANIC MATERIALS X, 2010, 7774
[4]   EXPERIMENTAL DEMONSTRATION OF THE DEPENDENCE OF THE 1ST HYPERPOLARIZABILITY OF DONOR-ACCEPTOR-SUBSTITUTED POLYENES ON THE GROUND-STATE POLARIZATION AND BOND-LENGTH ALTERNATION [J].
BOURHILL, G ;
BREDAS, JL ;
CHENG, LT ;
MARDER, SR ;
MEYERS, F ;
PERRY, JW ;
TIEMANN, BG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2619-2620
[5]   Fundamental aspects of property tuning in push-pull molecules [J].
Bures, Filip .
RSC ADVANCES, 2014, 4 (102) :58826-58851
[6]   Large electro-optic activity and enhanced thermal stability from diarylaminophenyl-containing high-β nonlinear optical chromophores [J].
Cheng, Yen-Ju ;
Luo, Jingdong ;
Hau, Steven ;
Bale, Denise H. ;
Kim, Tae-Dong ;
Shi, Zhengwei ;
Lao, David B. ;
Tucker, Neil M. ;
Tian, Yanqing ;
Dalton, Larry R. ;
Reid, Philip J. ;
Jen, Alex K-Y. .
CHEMISTRY OF MATERIALS, 2007, 19 (05) :1154-1163
[7]   Theory-inspired nano-engineering of photonic and electronic materials: Noncentro symmetric charge-transfer electro-optic materials [J].
Dalton, Larry R. ;
Sullivan, Philip A. ;
Bale, Denise H. ;
Bricht, Ben C. .
SOLID-STATE ELECTRONICS, 2007, 51 (10) :1263-1277
[8]   Electric Field Poled Organic Electro-optic Materials: State of the Art and Future Prospects [J].
Dalton, Larry R. ;
Sullivan, Philip A. ;
Bale, Denise H. .
CHEMICAL REVIEWS, 2010, 110 (01) :25-55
[9]   Novel Styrylquinolinium Dye Thin Films Deposited by Pulsed Laser Deposition for Nonlinear Optical Applications [J].
El Ouazzani, H. ;
Dabos-Seignon, Sylvie ;
Gindre, D. ;
Iliopoulos, K. ;
Todorova, M. ;
Bakalska, R. ;
Penchev, P. ;
Sotirov, S. ;
Kolev, Ts ;
Serbezov, V. ;
Arbaoui, A. ;
Bakasse, M. ;
Sahraoui, B. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2012, 116 (12) :7144-7152
[10]   Zinc Induced a Dramatic Enhancement of the Nonlinear Optical Properties of an Azo-Based Iminopyridine Ligand [J].
Guezguez, Imen ;
Ayadi, Awatef ;
Ordon, Karolina ;
Iliopoulos, Konstantinos ;
Branzea, Diana G. ;
Migalska-Zalas, Anna ;
Makowska-Janusik, Malgorzata ;
El-Ghayoury, Abdelkrim ;
Sahraoui, Bouchta .
JOURNAL OF PHYSICAL CHEMISTRY C, 2014, 118 (14) :7545-7553