Synthesis and Photophysical Studies of Naphthalene Diimide-based[3]Rotaxanes

doi:10.6023/A18070258

Acta Chim. Sinica ›› 2018, Vol. 76 ›› Issue (10): 779-784.DOI: 10.6023/A18070258 Previous Articles Next Articles

Article

萘二酰亚胺[3]轮烷的设计合成及发光性能研究

孙才力^a,b, 滕坤旭^a, 牛丽亚^a, 陈玉哲^b, 杨清正^a

a 北京师范大学化学学院放射性药物教育部重点实验室北京 100875;
b 中国科学院理化技术研究所光化学转换与功能材料重点实验室北京 100190

投稿日期:2018-07-04 发布日期:2018-08-13
通讯作者: 陈玉哲, 杨清正 E-mail:chenyuzhe@mail.ipc.ac.cn;qzyang@bnu.edu.cn
基金资助:
项目受国家自然科学基金（Nos.21525206，21561130149 and 21474124）和牛顿高级学者基金资助.

Synthesis and Photophysical Studies of Naphthalene Diimide-based[3]Rotaxanes

Sun Cai-Li^a,b, Teng Kun-Xu^a, Niu Li-Ya^a, Chen Yu-Zhe^b, Yang Qing-Zheng^a

a Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875;
b Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190

Received:2018-07-04 Published:2018-08-13
Contact: 10.6023/A18070258 E-mail:chenyuzhe@mail.ipc.ac.cn;qzyang@bnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21525206, 21561130149 and 21474124) and the Newton Advanced Fellowship.

1. Synthesis and Photophysical Studies of Naphthalene Diimide-based[3]Rotaxanes.PDF(1214KB)

Abstract

Rotaxanes, composed of macrocyclic wheel and linear axle, have been used in areas such as molecular machines, stimuli-responsive materials, information storage, supramolecular catalysts. The macrocyclic host and its noncovalent interaction are key for the rotaxanes. Pillar[n]arenes (n=5~10) have drew much attention as widely-used hosts. Their facile synthesis, unique rigid structure, versatile functionalization, and interesting host-guest properties enable pillar[n]arenes to build various supramolecular architectures including rotaxanes. Currently, the research of pillararene-based rotaxanes mainly focuses on the synthesis, the responsiveness to temperature and solvent, and the application as catalyst, however, reports of emissive pillararene-based rotaxanes are very rare. Besides, higher-ordered[n]rotaxanes (n ≥ 3) based on pillararene remain rarely explored limited by the poor synthetic yield, despite their fascinating structure and potential applications in molecular devices. Herein, we report two pillararene-based rotaxanes ([3]R and [3]R') incorporating naphthalene diimide with red fluorescence in solid state. The 1,4-diethoxypillar[5]arene (EtP5A) was chosen as the wheel, diamino-substituted naphthalene diimides (NDI) were used as the axle containing two separated linear guest parts for EtP5A. The addition reaction of NDI-precursor S1/S2 and the stopper 3,5-dimethylphenyl isocyanate with the presence of EtP5A afforded [3]R and[2]R (byproduct as model compound)/[3]R', respectively, with high yield of 45% for [3]R and 62% for [3]R'. The structures of rotaxanes were confirmed by ¹H NMR spectroscopy, ROESY (rotating frame Overhause enhancement spectroscopy), and HR-ESI-MS. Limited by the length of linear chains, EtP5As are adjacent tightly to NDI in [3]R, whereas EtP5As stay four-atom distance away from NDI in 3[R]'. The optical properties of rotaxanes in various solvents and in powders were detected. [3]R and [3]R' show bright red fluorescence not only in solution but also in solid state, which distinguishes [3]R and [3]R' from [2]R and most of NDI-based fluorescent compounds. The increased fluorescence in solid state of [3]R and [3]R' benefits from the bulky EtP5As hindering the π-π interaction and suppressing the self-quenching of NDI. We suspect that [3]R and [3]R' may have potential applications in red-emitting materials and optoelectronic devices.

Key words: rotaxane, pillararene, fluorescence, naphthalene diimide

Cite this article

Sun Cai-Li, Teng Kun-Xu, Niu Li-Ya, Chen Yu-Zhe, Yang Qing-Zheng. Synthesis and Photophysical Studies of Naphthalene Diimide-based[3]Rotaxanes[J]. Acta Chim. Sinica, 2018, 76(10): 779-784.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Xue, M.; Yang, Y.; Chi, X.; Yan, X.; Huang, F. Chem. Rev. 2015, 115, 7398.
[2] (a) Yang, W.; Li, Y.; Liu, H.; Chi, L.; Li, Y. Small 2012, 8, 504.
(b) van Dongen, S. F.; Cantekin, S.; Elemans, J. A.; Rowan, A. E.; Nolte, R. J. Chem. Soc. Rev. 2014, 43, 99.
(c) Qu, D. H.; Wang, Q. C.; Zhang, Q. W.; Ma, X.; Tian, H. Chem. Rev. 2015, 115, 7543.
(d) Erbas-Cakmak, S.; Leigh, D. A.; McTernan, C. T.; Nussbaumer, A. L. Chem. Rev. 2015, 115, 10081.
(e) Han, X.; Li, Z.; Xu, Z.; Zhao, Z.; Liu, S. H.; Yin, J. Chin. J. Chem. 2017, 35, 1050.
(f) Lu, Y.; Liang, D.-D.; Fu, Z.-D.; Guo, Q.-H.; Wang, M.-X. Chin. J. Chem. 2018, 36, 630.
[3] Qu, D.-H.; Ji, F.-Y.; Wang, Q.-C.; Tian, H. Adv. Mater. 2006, 18, 2035.
[4] Meng, Z.; Xiang, J.-F.; Chen, C.-F. Chem. Sci. 2014, 5, 1520.
[5] Wang, Y.; Tian, Y.; Chen, Y.-Z.; Niu, L.-Y.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z.; Boulatov, R. Chem. Commun. 2018, 54, 7991.
[6] Green, J. E.; Choi, J. W.; Boukai, A.; Bunimovich, Y.; John-ston-Halperin, E.; DeIonno, E.; Luo, Y.; Sheriff, B. A.; Xu, K.; Shin, Y. S.; Tseng, H.-R.; Stoddart, J. F.; Heath, J. R. Nature 2007, 445, 414.
[7] Lewandowski, B.; De Bo, G.; Ward, J. W.; Papmeyer, M.; Kuschel, S.; Aldegunde, M. J.; Gramlich, P. M.; Heckmann, D.; Goldup, S. M.; D'Souza, D. M.; Fernandes, A. E.; Leigh, D. A. Science 2013, 339, 189.
[8] (a) Yue, S.; Zhou, Y.; Yao, Y.; Xue, M. Acta Chim. Sinica 2014, 72, 1053(in Chinese). (岳诗雨, 周玉娟, 姚勇, 薛敏, 化学学报, 2014, 72, 1053.)
(b) Ogoshi, T.; Yamagishi T.; Nakamoto, Y. Chem. Rev. 2016, 116, 7937.
[9] Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022.
[10] (a) Hu, X.-B.; Chen, L.; Si, W.; Yu, Y.; Hou, J.-L. Chem. Commun. 2011, 47, 4694.
(b) Li, S.-H.; Zhang, H.-Y.; Xu, X.; Liu, Y. Nat. Commun. 2015, 6, 7590.
(c) Sun, C.-L.; Xu, J.-F.; Chen, Y.-Z.; Niu, L.-Y.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. Chin. Chem. Lett. 2015, 26, 843.
(d) Zhou, Y.; Jie, K.; Shi, B.; Yao, Y. Chem. Commun. 2015, 51, 11112.
(e) Tan, L. L.; Li, H.; Tao, Y.; Zhang, S. X.-A.; Wang, B.; Yang, Y.-W. Adv. Mater. 2014, 26, 7027.
(f) Sun, C.-L.; Xu, J.-F., Chen, Y.-Z.; Niu, L.-Y.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. Polym. Chem. 2016. 7, 2057.
(g) Ma, L.; Wang, S.; Li, C.; Cao, D.; Li, T.; Ma, X. Chem. Commun. 2018, 54, 2405.
(h) Sun, C.-L.; Peng, H.-Q.; Niu, L.-Y.; Chen, Y.-Z.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. Chem. Commun. 2018, 54, 1117.
(i) Song, N.; Kakuta, T.; Yamagishi, T.; Yang, Y.-W.; Ogoshi, T. 10. 1016/j. chempr. 2018. 05. 015.
(j) Wu, J.-R.; Mu, A. U.; Li, B.; Wang, C.-Y.; Fang, L.; Yang, Y.-W. Angew. Chem. Int. Ed. 2018, 57, 9853.
[11] (a) Chang, Y.; Yang, K.; Wei, P.; Huang, S.; Pei, Y.; Zhao, W.; Pei, Z. Angew. Chem. Int. Ed. 2014, 53, 13126.
(b) Li, Z.-Y.; Zhang, Y.; Zhang, C.-W.; Chen, L.-J.; Wang, C.; Tan, H.; Yu, Y.; Li, X.; Yang, H.-B. J. Am. Chem. Soc. 2014, 136, 8577.
(c) Yuan, B.; Xu, J.-F.; Sun, C.-L.; Nicolas, H.; Schönhoff, M.; Yang, Q.-Z.; Zhang, X. ACS Appl. Mater. Interfaces 2015, 8, 3679.
(d) Zhang, M.; Zhu, P.-P.; Xin, P.; Si, W.; Li, Z.-T.; Hou, J.-L. Angew. Chem. Int. Ed. 2017, 56, 2999.
(e) Hao, Q.; Chen, Y.; Huang, Z.; Xu, J.-F.; Sun, Z.; Zhang, X. ACS Appl. Mater. Interfaces 2018, 10, 5365.
(f) Wang, S.; Xu, Z.; Wang, T.; Xiao, T.; Hu, X.-Y.; Shen, Y.-Z.; Wang, L. Nat. Commun. 2018, 9, 1737.
(g) Jie, K.; Zhou, Y.; Li, E.; Li, Z.; Zhao, R.; Huang, F. J. Am. Chem. Soc. 2017, 139, 15320.
(h) Jie, K.; Zhou, Y.; Li, E.; Zhao, R.; Liu, M.; Huang, F. J. Am. Chem. Soc. 2018, 140, 3190.
(i) Yang, K.; Wen, J.; Chao, S.; Liu, J.; Yang, K.; Pei, Y.; Pei, Z. Chem. Commun. 2018, 54, 5911.
(j) Sun, C.-L.; Gao, Z.; Teng, K.-X.; Niu, L.-Y.; Chen, Y.-Z.; Zhao, Y. S.; Yang, Q.-Z. ACS Appl. Mater. Interfaces 10.1021/acsami.8b08490.
[12] Strutt, N. L.; Forgan, R. S.; Spruell, J. M.; Botros, Y. Y.; Stoddart, J. F. J. Am. Chem. Soc. 2011, 133, 5668.
[13] Zhang, Z.; Han, C.; Yu, G.; Huang, F. Chem. Sci. 2012, 3, 3026.
[14] Ogoshi, T.; Aoki, T.; Shiga, R.; Iizuka, R.; Ueda, S.; Demachi, K.; Yamafuji, D.; Kayama, H.; Yamagishi, T. J. Am. Chem. Soc. 2012, 134, 20322.
[15] (a) Hu, X.-Y.; Wu, X.; Duan, Q.; Xiao, T.; Lin, C.; Wang, L. Org. Lett. 2012, 14, 4826.
(b) Wu, X.; Duan, Q.; Ni, M.; Hu, X.; Wang, L. Chin. J. Org. Chem. 2014, 34, 437(in Chinese). (吴旋, 段群鹏, 倪梦飞, 胡晓玉, 王乐勇, 有机化学, 2014, 34, 437.)
(c) Dong, S.; Yuan, J.; Huang, F. Chem. Sci. 2014, 5, 247.
(d) Du, X.-S.; Wang, C.-Y.; Jia, Q.; Deng, R.; Tian, H.-S.; Zhang, H.-Y.; Meguellati, K.; Yang, Y.-W. Chem. Commun. 2017, 53, 5326.
(e) Wang, S.; Shao, X.; Cai, W. J. Phys. Chem. C 2017, 121, 25547.
(f) Nierengarten, I.; Meichsner, E.; Holler, M.; Pieper, P.; Deschenaux, R.; Delavaux-Nicot, B.; Nierengarten, J.-F. Chem.-Eur. J. 2018, 24, 169.
[16] (a) Ma, X.; Tian, H. Chem. Soc. Rev. 2010, 39, 70.
(b) Ogoshi, T.; Yamafuji, D.; Yamagishi, T.; Brouwer, A. M. Chem. Commun. 2013, 49, 5468.
(c) Sun, N.; Xiao, X.; Li, W.; Jiang, J. Adv. Sci. 2015, 2, 1500082.
(d) Yu, G.; Wu, D.; Li, Y.; Zhang, Z.; Shao, L.; Zhou, J.; Hu, Q.; Tang, G.; Huang, F. Chem. Sci. 2016, 7, 3017.
(e) Delavaux-Nicot, B.; Ben Aziza, H.; Nierengarten, I.; Minh Nguyet Trinh, T.; Meichsner, E.; Chessé, M.; Holler, M.; Abidi, R.; Maisonhaute, E.; Nierengarten, J.-F. Chem. Eur. J. 2018, 24, 133.
[17] (a) Ogoshi, T.; Yamafuji, D.; Aoki, T.; Kitajima, K.; Yamagishi, T.; Hayashi, Y.; Kawauchi, S. Chem. Eur. J. 2012, 18, 7493.
(b) Ke, C.; Strutt, N. L.; Li, H.; Hou, X.; Hartlieb, K. J.; McGonigal, P. R.; Ma, Z.; Iehl, J.; Stern, C. L.; Cheng, C.; Zhu, Z.; Vermeulen, N. A.; Meade, T. J.; Botros, Y. Y.; Stoddart, J. F. J. Am. Chem. Soc. 2013, 135, 17019.
(c) Hou, X.; Ke, C.; Cheng, C.; Song, N.; Blackburn, A. K.; Sarjeant, A. A.; Botros, Y. Y.; Yang, Y. W.; Stoddart, J. F. Chem. Commun. 2014, 50, 6196.
[18] Suraru, S.-L.; Würthner, F. Angew. Chem. Int. Ed. 2014, 53, 7428.
(b) Fan, W.; Liu, C.; Li, Y.; Wang, Z. Chem. Commun. 2017, 53, 188.
(c) Shi, Y.; Ni, Z.; Zhen, Y.; Dong, H.; Hu, W. Chin. J. Org. Chem. 2016, 36, 1741(in Chinese). (石燕君, 倪振杰, 甄永刚, 董焕丽, 胡文平, 有机化学, 2016, 36, 1741.).
(d) Jia, T.; Zheng, N.; Cai, W.; Ying, L.; Huang, F. Acta Chim. Sinica 2017, 75, 808(in Chinese). (贾涛, 郑楠楠, 蔡万清, 应磊, 黄飞, 化学学报, 2017, 75, 808.)
[19] (a) Würthner, F.; Ahmed, S.; Thalacker, C.; Debaerdemaeker, T. Chem. Eur. J. 2002, 8, 4742.
(b) Sakai, N.; Mareda, J.; Vauthey, E.; Matile, S. Chem. Commun. 2010, 46, 4225.
[20] Ogoshi, T.; Kitajima, K.; Aoki, T.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y. J. Org. Chem. 2010, 75, 3268.

萘二酰亚胺[3]轮烷的设计合成及发光性能研究

Synthesis and Photophysical Studies of Naphthalene Diimide-based[3]Rotaxanes

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Feida Che, Xiaoming Zhao, Xin Zhang, Qi Ding, Xin Wang, Ping Li, Bo Tang. Fluorescence Imaging of Active Molecules Associated with Depression^★ [J]. Acta Chimica Sinica, 2023, 81(9): 1255-1264.
[2]	Yinuo Wang, Shiyang Shao, Lixiang Wang. Recent Advances in Multiple Resonance Organic/Polymer Fluorescent Materials with Narrowband Emission^★ [J]. Acta Chimica Sinica, 2023, 81(9): 1202-1214.
[3]	Fengjie Ge, Kaizhi Zhang, Qingpeng Cao, Hui Xu, Tao Zhou, Wenhao Zhang, Xinxin Ban, Xiaobo Zhang, Na Li, Peng Zhu. Design, Synthesis and Electroluminescence Performance of Flexible Fluorenyl Block Delayed Fluorescence Dimers [J]. Acta Chimica Sinica, 2023, 81(9): 1157-1166.
[4]	Hongyue Wu, Rui Guo, Hanwen Chi, Yonghe Tang, Sirui Song, Enxiang Ge, Weiying Lin. Viscosity Fluorescent Probes Based on Quinoline Group and Its Applications [J]. Acta Chimica Sinica, 2023, 81(8): 905-911.
[5]	Xiao Wang, Xingwen Wang, Lehui Xiao. Nanocatalytic Mechanisms Investigated by Single Molecule Fluorescence Imaging at the Single-Particle Level [J]. Acta Chimica Sinica, 2023, 81(8): 1002-1014.
[6]	Wenshan Zheng, Guanbin Gao, Hao Deng, Taolei Sun. Room Temperature Synthesis and Near-infrared Fluorescence Performance Optimization of Ag₂Se@Ag₂S Core-shell Quantum Dots [J]. Acta Chimica Sinica, 2023, 81(7): 763-770.
[7]	Zhenyu Liu, Junfeng Rao, Shoujia Zhu, Bingyang Wang, Fan Yu, Quanyou Feng, Linghai Xie. Research Progress of Solution-Processed Self-Host Thermally Activated Delayed Fluorescence Materials [J]. Acta Chimica Sinica, 2023, 81(7): 820-835.
[8]	Yinfeng Wang, Meng Li, Chuanfeng Chen. Chiral Triptycene-Based Red Thermally Activated Delayed Fluorescence Polymers and Their Organic Light-Emitting Diodes^★ [J]. Acta Chimica Sinica, 2023, 81(6): 588-594.
[9]	Changshun Ma, Weihang Jin, Fei Tong, Ruirui Gu, Dahui Qu. Synthesis and Characterization of a Novel Pillar[5]arene That can Undergo Single-Crystal-to-Single-Crystal (SCSC) Transformation^★ [J]. Acta Chimica Sinica, 2023, 81(6): 572-576.
[10]	Xin Lv, Yi Wu, Boran Zhang, Wei Guo. Design, Synthesis and Photodynamic Therapy of a H₂O₂-Activatable Near Infrared Borondipyrromethene （BODIPY） Photosensitizer [J]. Acta Chimica Sinica, 2023, 81(4): 359-370.
[11]	Shaoqin Zhang, Meiqing Li, Zhongjun Zhou, Zexing Qu. Theoretical Study on the Multiple Resonance Thermally Activated Delayed Fluorescence Process [J]. Acta Chimica Sinica, 2023, 81(2): 124-130.
[12]	Yanqin Huang, Lijun Li, Shupei Yang, Rui Zhang, Xingfen Liu, Quli Fan, Wei Huang. HA-AuNPs/FDF for Highly Sensitive Detection of Hyaluronidase, Tumor-targeting Fluorescence Cell Imaging and Phototherapy [J]. Acta Chimica Sinica, 2023, 81(12): 1687-1694.
[13]	Dongxu Li, Xiang Xu, Jiage Song, Songting Liang, Yuang Fu, Xinhui Lu, Yingping Zou. Rotaxane Structure Optimizes the Photovoltaic Performance of Polymer Solar Cells^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1500-1507.
[14]	Li Sun, Yajing Wang, Tao Li, Yingshu Guo, Shusheng Zhang. Au Nanocages Probes for Mitochondrial Imaging and Photothermal Damage Cells^★ [J]. Acta Chimica Sinica, 2023, 81(10): 1301-1310.
[15]	Sirui Song, Yonghe Tang, Liangguang Sun, Rui Guo, Guanfan Jiang, Weiying Lin. Development of a Novel Fluorescent Probe Based on Coumarin Fluorophore for Polarity Detection and Its Imaging Applications [J]. Acta Chimica Sinica, 2022, 80(9): 1217-1222.