Citation: 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 Chimica Sinica, ;2018, 76(10): 779-784. doi: 10.6023/A18070258 shu

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

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

Corresponding author: Chen Yu-Zhe, chenyuzhe@mail.ipc.ac.cn Yang Qing-Zheng, qzyang@bnu.edu.cn
Received Date: 4 July 2018
Available Online: 13 October 2018
Fund Project: the National Natural Science Foundation of China 21561130149the National Natural Science Foundation of China 21525206the National Natural Science Foundation of China 21474124Project supported by the National Natural Science Foundation of China (Nos. 21525206, 21561130149 and 21474124) and the Newton Advanced Fellowship

Figures(7)

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.
- rotaxane,
- pillararene,
- fluorescence,
- naphthalene diimide
1. [1]
  Xue, M.; Yang, Y.; Chi, X.; Yan, X.; Huang, F. Chem. Rev. 2015, 115, 7398. doi: 10.1021/cr5005869
2. [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. [3]
  Qu, D.-H.; Ji, F.-Y.; Wang, Q.-C.; Tian, H. Adv. Mater. 2006, 18, 2035. doi: 10.1002/(ISSN)1521-4095
4. [4]
  Meng, Z.; Xiang, J.-F.; Chen, C.-F. Chem. Sci. 2014, 5, 1520. doi: 10.1039/c3sc53295j
5. [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. doi: 10.1039/C8CC04542A
6. [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. doi: 10.1038/nature05462
7. [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. doi: 10.1126/science.1229753
8. [8]
9. [9]
  Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022. doi: 10.1021/ja711260m
10. [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. [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. [12]
  Strutt, N. L.; Forgan, R. S.; Spruell, J. M.; Botros, Y. Y.; Stoddart, J. F. J. Am. Chem. Soc. 2011, 133, 5668. doi: 10.1021/ja111418j
13. [13]
  Zhang, Z.; Han, C.; Yu, G.; Huang, F. Chem. Sci. 2012, 3, 3026. doi: 10.1039/c2sc20728a
14. [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. doi: 10.1021/ja310757p
15. [15]
16. [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. [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. [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. [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. [20]
  Ogoshi, T.; Kitajima, K.; Aoki, T.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y. J. Org. Chem. 2010, 75, 3268. doi: 10.1021/jo100273n
1. [1]
  YanYuan Jia , Rong Rong , Jie Liu , Jing Guo , GuoYu Jiang , Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035
2. [2]
  Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
3. [3]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
4. [4]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
5. [5]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
6. [6]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
7. [7]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242
8. [8]
  Xinyu Liu , Weiran Hu , Zhengkai Li , Wei Ji , Xiao Ni . Algin Lab: Surging Luminescent Sea. University Chemistry, 2024, 39(5): 396-404. doi: 10.3866/PKU.DXHX202312021
9. [9]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
10. [10]
  Jiarui Wu , Gengxin Wu , Yan Wang , Yingwei Yang . Crystal Engineering Based on Leaning Towerarenes. University Chemistry, 2024, 39(3): 58-62. doi: 10.3866/PKU.DXHX202304014
11. [11]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
12. [12]
  Chun-Lin Sun , Yaole Jiang , Yu Chen , Rongjing Guo , Yongwen Shen , Xinping Hui , Baoxin Zhang , Xiaobo Pan . Construction, Performance Testing, and Practical Applications of a Home-Made Open Fluorescence Spectrometer. University Chemistry, 2024, 39(5): 287-295. doi: 10.3866/PKU.DXHX202311096
13. [13]
  Jianjun Liu , Xue Yang , Chi Zhang , Xueyu Zhao , Zhiwei Zhang , Yongmei Chen , Qinghong Xu , Shao Jin . Preparation and Fluorescence Characterization of CdTe Semiconductor Quantum Dots. University Chemistry, 2024, 39(7): 307-315. doi: 10.3866/PKU.DXHX202311031
14. [14]
  Zishuo Yi , Peng Liu , Yan Xu . Fluorescent “Chameleon”: A Popular Science Experiment Based on Dynamic Luminescence. University Chemistry, 2024, 39(9): 304-310. doi: 10.12461/PKU.DXHX202311079
15. [15]
  Jiaxin Su , Jiaqi Zhang , Shuming Chai , Yankun Wang , Sibo Wang , Yuanxing Fang . Optimizing Poly(heptazine imide) Photoanodes Using Binary Molten Salt Synthesis for Water Oxidation Reaction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408012-. doi: 10.3866/PKU.WHXB202408012
16. [16]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
17. [17]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
18. [18]
  Xinyi Hong , Tailing Xue , Zhou Xu , Enrong Xie , Mingkai Wu , Qingqing Wang , Lina Wu . Non-Site-Specific Fluorescent Labeling of Proteins as a Chemical Biology Experiment. University Chemistry, 2024, 39(4): 351-360. doi: 10.3866/PKU.DXHX202310010
19. [19]
  Lin Song , Dourong Wang , Biao Zhang . Innovative Experimental Design and Research on Preparing Flexible Perovskite Fluorescent Gels Using 3D Printing. University Chemistry, 2024, 39(7): 337-344. doi: 10.3866/PKU.DXHX202310107
20. [20]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(1321)
HTML views(304)

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