Citation: Bo Yifan, Liu Yuyu, Chang Yongzheng, Li Yinxiang, Zhang Xiaofei, Song Chunyuan, Xu Weifeng, Cao Hongtao, Huang Wei. Theoretical and Experimental Studies on Raman Spectroscopy of Cyclic Fluorene-Based Strained Semiconductors[J]. Acta Chimica Sinica, ;2019, 77(5): 442-446. doi: 10.6023/A19010005 shu

Theoretical and Experimental Studies on Raman Spectroscopy of Cyclic Fluorene-Based Strained Semiconductors

Bo Yifan ^a,† ,
Liu Yuyu ^a,† ,
Chang Yongzheng ^a,, ,
Li Yinxiang ^a ,
Zhang Xiaofei ^b ,
Song Chunyuan ^a ,
Xu Weifeng ^c ,
Cao Hongtao ^a,, ,
Huang Wei ^a,b,,

a.
Key Laboratory for Organic Electronics and Information Displays & Institute of Advanced Materials(IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing University of Posts & Telecommunications, Nanjing 210023, China
b.
College of Mathematics and Information Science, Guangxi University, Nanning 530004, China
c.
Nanjing Huadong Electronic Information Technology Co., Ltd., Nanjing 210033, China
d.
Shaanxi Institute of Flexible Electronics(SIFE), Northwestern Polytechnical University(NPU), Xi'an 710072, China

Corresponding author: Chang Yongzheng, iamyzchang@njupt.edu.cn Cao Hongtao, iamhtcao@njupt.edu.cn Huang Wei, iamwhuang@njupt.edu.cn

^†

Supporting information

http://sioc-journal.cn

Received Date: 2 January 2019
Available Online: 25 May 2019
Fund Project: the National Natural Science Foundation of China 61605090Natural Science Foundation of Jiangsu Province of China BK20180751Natural Science Foundation of Jiangsu Province of China BK20150832The Nanjing University of Post and Telecommunications NY217082Doctoral Fund of Ministry of Education of China 20133223110007Project supported by the National Natural Science Foundation of China (Nos. 21503114, 21602111, 61605090), Doctoral Fund of Ministry of Education of China (20133223110007), Natural Science Foundation of Jiangsu Province of China (BK20150832, BK20180751), The Nanjing University of Post and Telecommunications (NY217082), Synergetic Innovation Center for Organic Electronics and Information Displays and Excellent science and technology innovation team of Jiangsu Higher Education Institutions (2013). Project was funded by the Priority Academic Program Development of Jiangsu Higher Education Institutionsthe National Natural Science Foundation of China 21602111the National Natural Science Foundation of China 21503114

Figures(6)

Cyclic fluorene-based strained semiconductors which achieve both merits of hoop-shaped cycloparaphenylenes and fluorene-based emitters with high-efficiency feature have attracted increasing attention from synthetic chemists and theoreticians due to their aesthetic molecular structure, radial p orbitals and nanosized cavities. Compared with linear fluorene-based semiconductors, Cyclic fluorene-based strained semiconductors exhibit unique photoelectrical properties. For example, contrary to the deep blue emission of linear fluorene-based molecules, the controlled cyclic fluorene-based strained molecules show stronger green emission. However, the properties of molecular vibrations of cyclic fluorene-based strained materials have not been reported so far. In this article, [4]Cyclo-9, 9-dipropyl-2, 7-fluorene (CF) and linear quaterfluorenes (LF) were synthesized as modeling compounds to explore the differences of Raman spectra on structures by theoretical and experimental studies. Raman spectroscopy measurements have been presented on polymer poly(9, 9-dioctylfluorene) (PFO) and LF, and compare them with CF. In addition, we have calculated the theoretical Raman spectra of CF and LF based on time-dependent density functional theory (TDDFT), which are then compared to the experimental results for the assignment of different modes. All calculations were performed at 6-31G (d) basis set along with the range corrected B3LYP density functional. The results demonstrate that the Raman peak positions of CF which are analogous to those of carbon nanotubes such as G band are shifted. Compared to the Raman spectra of LF, G₁ and G₂ peaks of CF shifted to lower frequency region, however G₃ peaks shifted to higher frequency region. The relative intensity of Raman peaks in CF especially in low frequency region has increased. These properties of Raman in CF can be assigned to the changed structure of conjugated backbone and electrical structure due to strain and every fluorene unit of CF has involved in vibration and the delocalization of π electrons gets higher. These results provide powerful basis for correlating structure and properties on strain organic semiconductors by Raman spectra.
- fluorene-based material,
- organic semiconductor,
- strained macrocycle,
- Raman spectrum,
- density functional theory calculation
1. [1]
  Xie, L. H.; Yin, C. R.; Lai, W. Y.; Fan, Q. L.; Huang, W. Prog. Polym. Sci. 2012, 37, 1192. doi: 10.1016/j.progpolymsci.2012.02.003
2. [2]
  Sun, M. L.; Xu, R. C.; Xie, L. H.; Wei, Y.; Huang, W. Chinese J. Chem. 2015, 33, 815. doi: 10.1002/cjoc.v33.8
3. [3]
  Qian, Y.; Zhang, X.; Xie, L. H.; Qi, D.; Chandran, B. K.; Chen, X.; Huang, W. Adv. Mater. 2016, 28, 9243. doi: 10.1002/adma.201601278
4. [4]
  Bao, Z. N.; Rogers, J. A.; Katz, H. E. J. Mater. Chem. 1999, 9, 1895. doi: 10.1039/a902652e
5. [5]
  Park, S.; Lee, M. H.; Ahn, K. S.; Choi, H. H.; Shin, J.; Xu, J.; Mei, J. G.; Cho, K.; Bao, Z. A.; Lee, D. R.; Kang, M. S.; Kim, D. H. Adv. Funct. Mater. 2016, 26, 4627. doi: 10.1002/adfm.v26.26
6. [6]
  Liu, Y.; Yuan, J.; Zou, Y. P.; Li, Y. F. Acta Chim. Sinica 2017, 75, 257. doi: 10.3969/j.issn.0253-2409.2017.03.001
7. [7]
  Songbuer; Li, M. H.; Imerhasan, M. Chin. J. Org. Chem. 2018, 38, 594.
8. [8]
  Yamago, S.; Kayahara, E.; Iwamoto, T. Chem. Rec. 2014, 14, 84. doi: 10.1002/tcr.v14.1
9. [9]
  Lewis, S. E. Chem. Soc. Rev. 2015, 44, 2221. doi: 10.1039/C4CS00366G
10. [10]
  Darzi, E. R.; Jasti, R. Chem. Soc. Rev. 2015, 44, 6401. doi: 10.1039/C5CS00143A
11. [11]
  Segawa, Y.; Yagi, A.; Itami, K. Phys. Sci. Rev. 2017, 2, 20160102.
12. [12]
  Kayahara, E.; Kouyama, T.; Kato, T.; Yamago, S. J. Am. Chem. Soc. 2016, 138, 338. doi: 10.1021/jacs.5b10855
13. [13]
  Liu, Y. Y.; Lin, J. Y.; Bo, Y. F.; Xie, L. H.; Yi, M. D.; Zhang, X. W.; Zhang, H. M.; Loh, T. P.; Huang, W. Org. Lett. 2016, 18, 172. doi: 10.1021/acs.orglett.5b03038
14. [14]
  Fujitsuka, M.; Cho, D. W.; Iwamoto, T.; Yamago, S.; Majima, T. Phys. Chem. Chem. Phys. 2012, 14, 14585. doi: 10.1039/c2cp42712e
15. [15]
  Segawa, Y.; Fukazawa, A.; Matsuura, S.; Omachi, H.; Yamaguchi, S.; Irle, S.; Itami, K. Org. Biomol. Chem. 2012, 10, 5979. doi: 10.1039/c2ob25199j
16. [16]
  Camacho, C.; Niehaus, T. A.; Itami, K.; Irle, S. Chem. Sci. 2013, 4, 187. doi: 10.1039/C2SC20878D
17. [17]
  Castiglioni, C.; Delzoppo, M.; Zerbi, G. J. Raman Spectrosc. 1993, 24, 485. doi: 10.1002/jrs.v24:8
18. [18]
  Rebelo, S. L.; Guedes, A.; Szefczyk, M. E.; Pereira, A. M.; Araujo, J. P.; Freire, C. Phys. Chem. Chem. Phys. 2016, 18, 12784. doi: 10.1039/C5CP06519D
19. [19]
  Moura, L. G.; Moutinho, M. V. O.; Venezuela, P.; Mauri, F.; Righi, A.; Strano, M. S.; Fantini, C.; Pimenta, M. A. Carbon 2017, 117, 41. doi: 10.1016/j.carbon.2017.02.048
20. [20]
  Piao, Y.; Simpson, J. R.; Streit, J. K.; Ao, G.; Zheng, M.; Fagan, J. A.; Hight Walker, A. R. ACS Nano 2016, 10, 5252. doi: 10.1021/acsnano.6b01031
21. [21]
  Fujitsuka, M.; Iwamoto, T.; Kayahara, E.; Yamago, S.; Majima, T. ChemPhysChem 2013, 14, 1570. doi: 10.1002/cphc.v14.8
22. [22]
  Chen, H.; Golder, M. R.; Wang, F.; Jasti, R.; Swan, A. K. Carbon 2014, 67, 203. doi: 10.1016/j.carbon.2013.09.082
23. [23]
  Alvarez, M. P.; Burrezo, P. M.; Kertesz, M.; Iwamoto, T.; Yamago, S.; Xia, J.; Jasti, R.; Navarrete, J. T. L.; Taravillo, M.; Baonza, V. G. Angew. Chem. Int. Ed. 2014, 53, 7033. doi: 10.1002/anie.201400719
24. [24]
  Chen, H.; Golder, M. R.; Wang, F.; Doorn, S. K.; Jasti, R.; Tretiak, S.; Swan, A. K. J. Phys. Chem. C 2015, 119, 2879. doi: 10.1021/jp5117195
25. [25]
  Pena-Alvarez, M.; Qiu, L.; Taravillo, M.; Baonza, V. G.; Delgado, M. C.; Yamago, S.; Jasti, R.; Navarrete, J. T.; Casado, J.; Kertesz, M. Phys. Chem. Chem. Phys. 2016, 18, 11683. doi: 10.1039/C5CP05500H
26. [26]
  Liu, Y. Y.; Li, J. W.; Bo, Y. F.; Yang, L.; Zhang, X. F.; Xie, L. H.; Yi, M. D.; Huang, W. Acta Phys.-Chim. Sin. 2017, 33, 1803.
27. [27]
  Ariu, M.; Lidzey, D. G.; Bradley, D. D. C. Synthetic Met. 2000, 111, 607.
28. [28]
  Arif, M.; Volz, C.; Guha, S. Phys. Rev. Lett. 2006, 96, 025503. doi: 10.1103/PhysRevLett.96.025503
29. [29]
  Volz, C.; Arif, M.; Guha, S. J. Chem. Phys. 2007, 126, 064905.
30. [30]
  Tsoi, W. C.; Lidzey, D. G. J. Phys. Condens. Mat. 2008, 20, 125213. doi: 10.1088/0953-8984/20/12/125213
31. [31]
  Liu, B.; Lin, J. Y.; Liu, F.; Yu, M. N.; Zhang, X. W.; Xia, R. D.; Yang, T.; Fang, Y. T.; Xie, L. H.; Huang, W. ACS Appl. Mater. Inter. 2016, 8, 21648. doi: 10.1021/acsami.6b05247
32. [32]
  Irle, S.; Lischka, H. J. Mol. Struc.-Theochem 1996, 364, 15. doi: 10.1016/0166-1280(95)04465-5
1. [1]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
2. [2]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
3. [3]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
4. [4]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
5. [5]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
6. [6]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
7. [7]
  Liang MA , Honghua ZHANG , Weilu ZHENG , Aoqi YOU , Zhiyong OUYANG , Junjiang CAO . Construction of highly ordered ZIF-8/Au nanocomposite structure arrays and application of surface-enhanced Raman spectroscopy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1743-1754. doi: 10.11862/CJIC.20240075
8. [8]
  Lina Feng , Guoyu Jiang , Xiaoxia Jian , Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171
9. [9]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
10. [10]
  Zhuomin Zhang , Hanbing Huang , Liangqiu Lin , Jingsong Liu , Gongke Li . Course Construction of Instrumental Analysis Experiment: Surface-Enhanced Raman Spectroscopy for Rapid Detection of Edible Pigments. University Chemistry, 2024, 39(2): 133-139. doi: 10.3866/PKU.DXHX202308034
11. [11]
  Jingyi Chen , Fu Liu , Tiejun Zhu , Kui Cheng . Practice of Integrating Ideological and Political Education into Raman Spectroscopy Analysis Experiment Course. University Chemistry, 2024, 39(2): 140-146. doi: 10.3866/PKU.DXHX202310111
12. [12]
  Wei Peng , Baoying Wen , Huamin Li , Yiru Wang , Jianfeng Li . Exploration and Practice on Raman Scattering Spectroscopy Experimental Teaching. University Chemistry, 2024, 39(8): 230-240. doi: 10.3866/PKU.DXHX202312062
13. [13]
  Zhaoyue Lü , Zhehao Chen , Yi Ni , Duanbin Luo , Xianfeng Hong . Multi-Level Teaching Design and Practice Exploration of Raman Spectroscopy Experiment. University Chemistry, 2024, 39(11): 304-312. doi: 10.12461/PKU.DXHX202402047
14. [14]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
15. [15]
  Xiaofang DONG , Yue YANG , Shen WANG , Xiaofang HAO , Yuxia WANG , Peng CHENG . Research progress of conductive metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 14-34. doi: 10.11862/CJIC.20240388
16. [16]
  Meng Lin , Heng Zhang , Shiling Yuan . Exploring a Combined Theory-Practice-Simulation Teaching Model in Physical Chemistry: A Case Study of Surface Tension. University Chemistry, 2025, 40(4): 189-194. doi: 10.12461/PKU.DXHX202407053
17. [17]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
18. [18]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
19. [19]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
20. [20]
  Yutong Dong , Huiling Xu , Yucheng Zhao , Zexin Zhang , Ying Wang . The Hidden World of Surface Tension and Droplets. University Chemistry, 2024, 39(6): 357-365. doi: 10.3866/PKU.DXHX202312022

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(1283)
HTML views(284)

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