Twistacene-modified heteroarenes: synthesis, characterization and optical limiting response

Zhang Jian; Song Yinglin; Yan Xiusheng; Xiao Jinchong

doi:10.3788/IRLA201948.1103005

Volume 48 Issue 11

Dec. 2019

Turn off MathJax

Article Contents

Article Navigation > Infrared and Laser Engineering > 2019 > 48(11): 1103005-1103005(7)

Zhang Jian, Song Yinglin, Yan Xiusheng, Xiao Jinchong. Twistacene-modified heteroarenes: synthesis, characterization and optical limiting response[J]. Infrared and Laser Engineering, 2019, 48(11): 1103005-1103005(7). doi: 10.3788/IRLA201948.1103005

Citation:

Zhang Jian, Song Yinglin, Yan Xiusheng, Xiao Jinchong. Twistacene-modified heteroarenes: synthesis, characterization and optical limiting response[J]. Infrared and Laser Engineering, 2019, 48(11): 1103005-1103005(7). doi: 10.3788/IRLA201948.1103005

Twistacene-modified heteroarenes: synthesis, characterization and optical limiting response

doi: 10.3788/IRLA201948.1103005

1.
College of Chemistry and Environmental Science,Key Laboratory of Chemical Biology of Hebei Province,Key Laboratory of Medicinal Chemistry and Molecular Diagnosis,Ministry of Education,Hebei University,Baoding 071002,China;
2.
Science and Technology on Electro-Optical Information Security Control Laboratory,Tianjin 300308,China;
3.
Department of Physics,Harbin Institute of Technology,Harbin 150001,China

Received Date: 2019-09-11
Rev Recd Date: 2019-10-21
Publish Date: 2019-11-25

Abstract

A series of novel twistace ne-decorated arenes including heterorings (2, 5, 8) were con-veniently synthesized promoted by palladium catalyst in one step and characterized. Compared with the model twistacene 1, all of them exhibited red-shifted absorption spectra with the maximum peaks centered at 462 nm for 2, 478 nm for 5, 468 nm for 8, and emission spectra spectra with the maximum bands at 476/506 nm for 2, 497/527 nm for 5, 497/520 nm for 8 respectively, which belonged to blue and green fluorescence region. The electrochemical properties were carried out through cyclic voltammetry method and molecule 8 displayed a smallest oxidation potential at 0.35 V among them, which resulted from the oxidation of the amine moiety. Their optical limiting properties were examined via femtosecond laser. The results suggest that all of them exhibit high transmittance and 5 possesses excellent optical limiting response.
- twistacene,
- synthesis,
- optoelectronic property,
- optical limiting

References

[1]	Getmanenko Yulia A, Allen Taylor G, Kim Hyeongeu, et al. Linear and third-order nonlinear optical properties of chalcogenopyrylium-terminated heptamethine dyes with rigid, bulky substituents[J]. Advanced Functional Materials, 2018, 28:1804073.
[2]	Hochberg Michael, Baehr-Jones Tom, Wang Guangxi, et al. Terahertz all-optical modulation in a silicon-polymer hybrid system[J]. Nature Materials, 2006, 5:703-709.
[3]	Gieseking Rebecca L, Mukhopadhyay Sukrit, Risko Chad, et al. Impact of the nature of the excited-state transition dipole moments on the third-order nonlinear optical response of polymethine dyes for all-optical switching applications[J]. ACS Photonics, 2014, 1:261-269.
[4]	Davydenko Iryna, Benis Sepehr, Shiring Stephen B, et al. Effects of meso-M(PPh3)2Cl (M=Pd, Ni) substituents on the linear and third-order nonlinear optical properties of chalcogenopyrylium-terminated heptamethines in solution and solid states[J]. Journal of Materials Chemistry C, 2018, 6:3613-3620.
[5]	Bao Qiaoliang, Zhang Han, Ni Zhenhua, et al. Monolayer graphene as a saturable absorber in a modelocked laser[J]. Nano Research, 2011, 4:297-307.
[6]	Rana Meenakshi, Singla Nidhi, Chatterjee Amrita, et al. Investigation of nonlinear optical (NLO) properties by charge transfer contributions of amine functionalized tetraphenylethylene[J]. Optical Materials, 2016, 62:80-89.
[7]	Chen Shulian, Xiao Jinchong, Zhang Xi, et al. Effect of the mismatch structure on crystal packing, physical properties and third-order nonlinearity of unsymmetrical twistacenes[J]. Dyes and Pigments, 2016, 134:9-18.
[8]	Li Dongxiang, Lin Weihong, Jiang Nengkai, et al. Optical limiting property of gold nanorods/ormosil gel glass composites[J]. Optical Communications, 2019, 437:363-366.
[9]	Su Huan, Zhu Senqiang, Qu Mingxing, et al. 1,3,5-Triazine-based Pt (II) metallogel material:synthesis, photophysical properties, and optical power-limiting performance[J]. The Journal of Physcical Chemistry C, 2019, 123:15685-15692.
[10]	Rao S Venugopal, Rao D Narayana, Akkara J A, et al. Dispersion studies of non-linear absorption in C60 using Z-scan[J]. Chemical Physics Letters, 1998, 297:491-498.
[11]	Wei T H, Hagan D J, Sence M J, et al. Direct measurements of nonlinear absorption and refraction in solutions of phthalocyanines[J]. Applied Physcics B:Laser and Optics, 1992, 54:46-51.
[12]	Xu Yanfei, Zhang Xiaoliang, Wang Yan, et al. A graphene hybrid material covalently functionalized with porphyrin:synthesis and optical limiting property[J]. Advanced Materials, 2009, 21:1275-1279.
[13]	Duong Hieu M, Bendikov Michael, Steiger Daniel, et al. Efficient synthesis of a novel, twisted and stable, electroluminescent twistacene[J]. Organic Letters, 2003, 5:4433-4436.
[14]	Chen Wangqiao, Li Xinxiong, Long Guankui, et al. Pyrene-containing twistarene:twelve benzene rings fused in a row[J]. Angewandte Chemie International Edition, 2018, 57:13555-13559.
[15]	Xiao Jinchong, Duong Hieu M, Liu Yi, et al. Synthesis and stru cture characterization of a stable nonatwistacene[J]. Angewandte Chemie International Edition, 2012, 51:6094-6098.
[16]	Xiao Jinchong, Malliakas Christos D, Liu Yi, et al. Clean reaction strategy to approach a stable, green heptatwistacene containing a single terminal pyrene unit[J]. Chemistry-An Asian Journal, 2012, 7:672-675.
[17]	Xiao Jinchong, Divayana Yoga, Doung Hieu M, et al. Synthesis, structure, and optoelectronic properties of a new twistacene 1,2,3,4,6,13-hexaphenyl-7:8,11:12-bisbenzo-pentacene[J]. Journal of Materials Chemistry, 2010, 20:8167-8170.
[18]	Zhang Xuemin, Li Shengliang, Liu Zhenying, et al. Self-assembled multicolor nanoparticles based on functionalized twistacene dendrimer for cell fluorescent imaging[J]. NPG Asia Materials, 2015, 7:e230.
[19]	Tian Feng, Song Tingting, Wang Tao, et al. 11,16-Di-tert-butyl-9,18-diphenylbenzo[kl]benzo[8,9] triphenyleno[2,3-b]xanthene:synthesis, photophysics, self-assembly and electroluminescent properties[J]. Asian Journal of Organic Chemistry, 2019, 8:399-403.
[20]	Zheng X, Feng M, Zhan H. Giant optical limiting effect in Ormosil gel glasses doped with graphene oxide materials[J]. Journal of Materials Chemistry C, 2013, 1:6759-6766.
[21]	Fu S, Zhu X, Zhou G, et al. Synthesis, structures and optical power limiting of some transition metal and lanthanide monoporphyrinate complexes containing electron-rich diphenylamino substituents[J]. European Journal of Inorganic Chemistry, 2007, 2007:2004-2013.
[22]	Zhang C, Song Y, Khn F E, et al. Ultrafast response and superior opt ical limiting effects of planar open heterothiometallic clusters[J]. Advanced Materials, 2002, 14:818-822.

Proportional views

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Get Citation

PDF

XML

Article Metrics

Article views(494) PDF downloads(48) Cited by()

Proportional views

Twistacene-modified heteroarenes: synthesis, characterization and optical limiting response

1. College of Chemistry and Environmental Science,Key Laboratory of Chemical Biology of Hebei Province,Key Laboratory of Medicinal Chemistry and Molecular Diagnosis,Ministry of Education,Hebei University,Baoding 071002,China;

2. Science and Technology on Electro-Optical Information Security Control Laboratory,Tianjin 300308,China;

3. Department of Physics,Harbin Institute of Technology,Harbin 150001,China

Received Date: 2019-09-11

Rev Recd Date: 2019-10-21

Publish Date: 2019-11-25

Key words:

Abstract: A series of novel twistace ne-decorated arenes including heterorings (2, 5, 8) were con-veniently synthesized promoted by palladium catalyst in one step and characterized. Compared with the model twistacene 1, all of them exhibited red-shifted absorption spectra with the maximum peaks centered at 462 nm for 2, 478 nm for 5, 468 nm for 8, and emission spectra spectra with the maximum bands at 476/506 nm for 2, 497/527 nm for 5, 497/520 nm for 8 respectively, which belonged to blue and green fluorescence region. The electrochemical properties were carried out through cyclic voltammetry method and molecule 8 displayed a smallest oxidation potential at 0.35 V among them, which resulted from the oxidation of the amine moiety. Their optical limiting properties were examined via femtosecond laser. The results suggest that all of them exhibit high transmittance and 5 possesses excellent optical limiting response.

HTML

Reference (22)

[1]	Getmanenko Yulia A, Allen Taylor G, Kim Hyeongeu, et al. Linear and third-order nonlinear optical properties of chalcogenopyrylium-terminated heptamethine dyes with rigid, bulky substituents[J]. Advanced Functional Materials, 2018, 28:1804073.
[2]	Hochberg Michael, Baehr-Jones Tom, Wang Guangxi, et al. Terahertz all-optical modulation in a silicon-polymer hybrid system[J]. Nature Materials, 2006, 5:703-709.
[3]	Gieseking Rebecca L, Mukhopadhyay Sukrit, Risko Chad, et al. Impact of the nature of the excited-state transition dipole moments on the third-order nonlinear optical response of polymethine dyes for all-optical switching applications[J]. ACS Photonics, 2014, 1:261-269.
[4]	Davydenko Iryna, Benis Sepehr, Shiring Stephen B, et al. Effects of meso-M(PPh3)2Cl (M=Pd, Ni) substituents on the linear and third-order nonlinear optical properties of chalcogenopyrylium-terminated heptamethines in solution and solid states[J]. Journal of Materials Chemistry C, 2018, 6:3613-3620.
[5]	Bao Qiaoliang, Zhang Han, Ni Zhenhua, et al. Monolayer graphene as a saturable absorber in a modelocked laser[J]. Nano Research, 2011, 4:297-307.
[6]	Rana Meenakshi, Singla Nidhi, Chatterjee Amrita, et al. Investigation of nonlinear optical (NLO) properties by charge transfer contributions of amine functionalized tetraphenylethylene[J]. Optical Materials, 2016, 62:80-89.
[7]	Chen Shulian, Xiao Jinchong, Zhang Xi, et al. Effect of the mismatch structure on crystal packing, physical properties and third-order nonlinearity of unsymmetrical twistacenes[J]. Dyes and Pigments, 2016, 134:9-18.
[8]	Li Dongxiang, Lin Weihong, Jiang Nengkai, et al. Optical limiting property of gold nanorods/ormosil gel glass composites[J]. Optical Communications, 2019, 437:363-366.
[9]	Su Huan, Zhu Senqiang, Qu Mingxing, et al. 1,3,5-Triazine-based Pt (II) metallogel material:synthesis, photophysical properties, and optical power-limiting performance[J]. The Journal of Physcical Chemistry C, 2019, 123:15685-15692.
[10]	Rao S Venugopal, Rao D Narayana, Akkara J A, et al. Dispersion studies of non-linear absorption in C60 using Z-scan[J]. Chemical Physics Letters, 1998, 297:491-498.
[11]	Wei T H, Hagan D J, Sence M J, et al. Direct measurements of nonlinear absorption and refraction in solutions of phthalocyanines[J]. Applied Physcics B:Laser and Optics, 1992, 54:46-51.
[12]	Xu Yanfei, Zhang Xiaoliang, Wang Yan, et al. A graphene hybrid material covalently functionalized with porphyrin:synthesis and optical limiting property[J]. Advanced Materials, 2009, 21:1275-1279.
[13]	Duong Hieu M, Bendikov Michael, Steiger Daniel, et al. Efficient synthesis of a novel, twisted and stable, electroluminescent twistacene[J]. Organic Letters, 2003, 5:4433-4436.
[14]	Chen Wangqiao, Li Xinxiong, Long Guankui, et al. Pyrene-containing twistarene:twelve benzene rings fused in a row[J]. Angewandte Chemie International Edition, 2018, 57:13555-13559.
[15]	Xiao Jinchong, Duong Hieu M, Liu Yi, et al. Synthesis and stru cture characterization of a stable nonatwistacene[J]. Angewandte Chemie International Edition, 2012, 51:6094-6098.
[16]	Xiao Jinchong, Malliakas Christos D, Liu Yi, et al. Clean reaction strategy to approach a stable, green heptatwistacene containing a single terminal pyrene unit[J]. Chemistry-An Asian Journal, 2012, 7:672-675.
[17]	Xiao Jinchong, Divayana Yoga, Doung Hieu M, et al. Synthesis, structure, and optoelectronic properties of a new twistacene 1,2,3,4,6,13-hexaphenyl-7:8,11:12-bisbenzo-pentacene[J]. Journal of Materials Chemistry, 2010, 20:8167-8170.
[18]	Zhang Xuemin, Li Shengliang, Liu Zhenying, et al. Self-assembled multicolor nanoparticles based on functionalized twistacene dendrimer for cell fluorescent imaging[J]. NPG Asia Materials, 2015, 7:e230.
[19]	Tian Feng, Song Tingting, Wang Tao, et al. 11,16-Di-tert-butyl-9,18-diphenylbenzo[kl]benzo[8,9] triphenyleno[2,3-b]xanthene:synthesis, photophysics, self-assembly and electroluminescent properties[J]. Asian Journal of Organic Chemistry, 2019, 8:399-403.
[20]	Zheng X, Feng M, Zhan H. Giant optical limiting effect in Ormosil gel glasses doped with graphene oxide materials[J]. Journal of Materials Chemistry C, 2013, 1:6759-6766.
[21]	Fu S, Zhu X, Zhou G, et al. Synthesis, structures and optical power limiting of some transition metal and lanthanide monoporphyrinate complexes containing electron-rich diphenylamino substituents[J]. European Journal of Inorganic Chemistry, 2007, 2007:2004-2013.
[22]	Zhang C, Song Y, Khn F E, et al. Ultrafast response and superior opt ical limiting effects of planar open heterothiometallic clusters[J]. Advanced Materials, 2002, 14:818-822.

Twistacene-modified heteroarenes: synthesis, characterization and optical limiting response

doi: 10.3788/IRLA201948.1103005

Abstract

References

Proportional views

通讯作者: 陈斌, bchen63@163.com

Article Metrics

Related

Proportional views