Modulating the Excited State Chirality of Dynamic Chemical Reactions in Chiral Micelles
Xuefeng Yang
CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, National Center for Nanoscience and Technology (NCNST) No.11, ZhongGuanCun BeiYiTiao, Beijing, 100190 P. R. China
University of Chinese Academy of Sciences, No.19(A) Yuquan Road, Shijingshan District, 100049 Beijing, P. R. China
Search for more papers by this authorDr. Xue Jin
CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, National Center for Nanoscience and Technology (NCNST) No.11, ZhongGuanCun BeiYiTiao, Beijing, 100190 P. R. China
Search for more papers by this authorLili Zhou
CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Zhongguancun North First Street 2, 100190 Beijing, P. R. China
Search for more papers by this authorCorresponding Author
Prof. Pengfei Duan
CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, National Center for Nanoscience and Technology (NCNST) No.11, ZhongGuanCun BeiYiTiao, Beijing, 100190 P. R. China
University of Chinese Academy of Sciences, No.19(A) Yuquan Road, Shijingshan District, 100049 Beijing, P. R. China
Search for more papers by this authorCorresponding Author
Dr. Yaxun Fan
CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Zhongguancun North First Street 2, 100190 Beijing, P. R. China
Search for more papers by this authorProf. Yilin Wang
CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Zhongguancun North First Street 2, 100190 Beijing, P. R. China
University of Chinese Academy of Sciences, No.19(A) Yuquan Road, Shijingshan District, 100049 Beijing, P. R. China
Search for more papers by this authorXuefeng Yang
CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, National Center for Nanoscience and Technology (NCNST) No.11, ZhongGuanCun BeiYiTiao, Beijing, 100190 P. R. China
University of Chinese Academy of Sciences, No.19(A) Yuquan Road, Shijingshan District, 100049 Beijing, P. R. China
Search for more papers by this authorDr. Xue Jin
CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, National Center for Nanoscience and Technology (NCNST) No.11, ZhongGuanCun BeiYiTiao, Beijing, 100190 P. R. China
Search for more papers by this authorLili Zhou
CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Zhongguancun North First Street 2, 100190 Beijing, P. R. China
Search for more papers by this authorCorresponding Author
Prof. Pengfei Duan
CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, National Center for Nanoscience and Technology (NCNST) No.11, ZhongGuanCun BeiYiTiao, Beijing, 100190 P. R. China
University of Chinese Academy of Sciences, No.19(A) Yuquan Road, Shijingshan District, 100049 Beijing, P. R. China
Search for more papers by this authorCorresponding Author
Dr. Yaxun Fan
CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Zhongguancun North First Street 2, 100190 Beijing, P. R. China
Search for more papers by this authorProf. Yilin Wang
CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Zhongguancun North First Street 2, 100190 Beijing, P. R. China
University of Chinese Academy of Sciences, No.19(A) Yuquan Road, Shijingshan District, 100049 Beijing, P. R. China
Search for more papers by this authorAbstract
Chirality generation and transfer is not only of critical importance in resolving the origin of biological homochirality, but also is of great significance for exploring the chirality-related functionalities in nanomaterials and supramolecular systems. Although modulating the ground state chirality in chiral nanomaterials has been widely demonstrated, it remains a big challenge to steer the excited state chirality (circularly polarized luminescence, CPL). Herein, we present a kind of chiral spherical micelles constructed by chiral cationic gemini surfactants, whose surfaces and cavities could co-assemble with hydrophilic and hydrophobic emitters concurrently. Subsequently, the hydrophilic and hydrophobic emitters could be endowed with CPL activity in the aqueous phase. Additionally, the cavities of such micelles can be regarded as the powerful chiral confined space, which could effectively modulate the excited state chirality of dynamic chemical reactions, enabling color-adjustable CPL emission.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
ange202115600-sup-0001-misc_information.pdf641.4 KB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aY. Sang, J. Han, T. Zhao, P. Duan, M. Liu, Adv. Mater. 2020, 32, 1900110;
- 1bM. Schadt, Annu. Rev. Mater. Sci. 1997, 27, 305;
- 1cY. Kim, B. Yeom, O. Arteaga, S. J. Yoo, S.-G. Lee, J.-G. Kim, N. A. Kotov, Nat. Mater. 2016, 15, 461;
- 1dY.-H. Kim, Y. Zhai, H. Lu, X. Pan, C. Xiao, E. A. Gaulding, S. P. Harvey, J. J. Berry, Z. V. Vardeny, J. M. Luther, M. C. Beard, Science 2021, 371, 1129;
- 1eR. Carr, N. H. Evans, D. Parker, Chem. Soc. Rev. 2012, 41, 7673–7686;
- 1fJ. Han, S. Guo, H. Lu, S. Liu, Q. Zhao, W. Huang, Adv. Opt. Mater. 2018, 6, 1800538;
- 1gD.-W. Zhang, M. Li, C.-F. Chen, Chem. Soc. Rev. 2020, 49, 1331–1343.
- 2X. Yang, X. Jin, T. Zhao, P. Duan, Mater. Chem. Front. 2021, 5, 4821–4832.
- 3G. Longhi, E. Castiglioni, J. Koshoubu, G. Mazzeo, S. Abbate, Chirality 2016, 28, 696–707.
- 4
- 4aJ. Roose, B. Z. Tang, K. S. Wong, Small 2016, 12, 6495–6512;
- 4bP. Sumsalee, L. Abella, T. Roisnel, S. Lebrequier, G. Pieters, J. Autschbach, J. Crassous, L. Favereau, J. Mater. Chem. C 2021, 9, 11905–11914;
- 4cH. Maeda, Y. Bando, K. Shimomura, I. Yamada, M. Naito, K. Nobusawa, H. Tsumatori, T. Kawai, J. Am. Chem. Soc. 2011, 133, 9266–9269;
- 4dK. Hayashi, Y. Miyaoka, Y. Ohishi, T.-a. Uchida, M. Iwamura, K. Nozaki, M. Inouye, Chem. Eur. J. 2018, 24, 14613–14616;
- 4eP. Liu, W. Chen, Y. Okazaki, Y. Battie, L. Brocard, M. Decossas, E. Pouget, P. Muller-Buschbaum, B. Kauffmann, S. Pathan, T. Sagawa, R. Oda, Nano Lett. 2020, 20, 8453–8460;
- 4fK. Takaishi, K. Iwachido, T. Ema, J. Am. Chem. Soc. 2020, 142, 1774–1779;
- 4gF. Zinna, S. Voci, L. Arrico, E. Brun, A. Homberg, L. Bouffier, T. Funaioli, J. Lacour, N. Sojic, L. Di Bari, Angew. Chem. Int. Ed. 2019, 58, 6952–6956; Angew. Chem. 2019, 131, 7026–7030;
- 4hY. Nojima, M. Hasegawa, N. Hara, Y. Imai, Y. Mazaki, Chem. Commun. 2019, 55, 2749–2752.
- 5
- 5aE. M. Sánchez-Carnerero, F. Moreno, B. L. Maroto, A. R. Agarrabeitia, M. J. Ortiz, B. G. Vo, G. Muller, S. de la Moya, J. Am. Chem. Soc. 2014, 136, 3346–3349;
- 5bE. M. Sánchez-Carnerero, A. R. Agarrabeitia, F. Moreno, B. L. Maroto, G. Muller, M. J. Ortiz, S. de la Moya, Chem. Eur. J. 2015, 21, 13488–13500.
- 6
- 6aZ. Huang, T. Jiang, J. Wang, X. Ma, H. Tian, Angew. Chem. Int. Ed. 2021, 60, 2855–2860; Angew. Chem. 2021, 133, 2891–2896;
- 6bS. Hu, L. Hu, X. Zhu, Y. Wang, M. Liu, Angew. Chem. Int. Ed. 2021, 60, 19451–19457; Angew. Chem. 2021, 133, 19600–19606;
- 6cJ. Wade, J. R. Brandt, D. Reger, F. Zinna, K. Y. Amsharov, N. Jux, D. L. Andrews, M. J. Fuchter, Angew. Chem. Int. Ed. 2021, 60, 222–227; Angew. Chem. 2021, 133, 224–229.
- 7Z. Wang, A. Hao, P. Xing, Small 2021, 17, 2104499.
- 8
- 8aY. Wu, C. Yan, X.-S. Li, L. H. You, Z.-Q. Yu, X. Wu, Z. Zheng, G. Liu, Z. Guo, H. Tian, W.-H. Zhu, Angew. Chem. Int. Ed. 2021, 60, 24549–24557; Angew. Chem. 2021, 133, 24754–24762;
- 8bY. Li, K. Liu, X. Li, Y. Quan, Y. Cheng, Chem. Commun. 2020, 56, 1117–1120;
- 8cX. Yang, M. Zhou, Y. Wang, P. Duan, Adv. Mater. 2020, 32, 2000820;
- 8dX. Yang, J. Han, Y. Wang, P. Duan, Chem. Sci. 2019, 10, 172.
- 9
- 9aY. Shi, P. Duan, S. Huo, Y. Li, M. Liu, Adv. Mater. 2018, 30, 1705011;
- 9bS. Huo, P. Duan, T. Jiao, Q. Peng, M. Liu, Angew. Chem. Int. Ed. 2017, 56, 12174–12178; Angew. Chem. 2017, 129, 12342–12346.
- 10
- 10aY. Ru, L. Sui, H. Song, X. Liu, Z. Tang, S.-Q. Zang, B. Yang, S. Lu, Angew. Chem. Int. Ed. 2021, 60, 14091–14099; Angew. Chem. 2021, 133, 14210–14218;
- 10bC.-T. Wang, K. Chen, P. Xu, F. Yeung, H.-S. Kwok, G. Li, Adv. Funct. Mater. 2019, 29, 1903155;
- 10cL. Wang, L. Yin, W. Zhang, X. Zhu, M. Fujiki, J. Am. Chem. Soc. 2017, 139, 13218–13226;
- 10dC. He, G. Yang, Y. Kuai, S. Shan, L. Yang, J. Hu, D. Zhang, Q. Zhang, G. Zou, Nat. Commun. 2018, 9, 5117;
- 10eC. He, Z. Feng, S. Shan, M. Wang, X. Chen, G. Zou, Nat. Commun. 2020, 11, 1188;
- 10fF. Li, Y. Wang, Z. Wang, Y. Cheng, C. Zhu, Polym. Chem. 2015, 6, 6802–6805;
- 10gS. An, A. Hao, P. Xing, Angew. Chem. Int. Ed. 2021, 60, 9902–9912; Angew. Chem. 2021, 133, 9990–10000.
- 11Q. Jiang, X. Xu, P.-A. Yin, K. Ma, Y. Zhen, P. Duan, Q. Peng, W.-Q. Chen, B. Ding, J. Am. Chem. Soc. 2019, 141, 9490–9494.
- 12
- 12aJ. Liang, P. Guo, X. Qin, X. Gao, K. Ma, X. Zhu, X. Jin, W. Xu, L. Jiang, P. Duan, ACS Nano 2020, 14, 3190–3198;
- 12bY. Zhang, D. Yang, J. Han, J. Zhou, Q. Jin, M. Liu, P. Duan, Langmuir 2018, 34, 5821–5830.
- 13L. Zhang, H.-X. Wang, S. Li, M. Liu, Chem. Soc. Rev. 2020, 49, 9095–9120.
- 14J. Han, J. You, X. Li, P. Duan, M. Liu, Adv. Mater. 2017, 29, 1606503.
- 15S. Paria, K. C. Khilar, Adv. Colloid Interface Sci. 2004, 110, 75–95.
- 16
- 16aT. Harada, N. Kajiyama, K. Ishizaka, R. Toyofuku, K. Izumi, K. Umemura, Y. Imai, N. Taniguchi, K. Mishima, Chem. Commun. 2014, 50, 11169–11172;
- 16bA. Sorrenti, O. Illa, R. M. Ortuno, Chem. Soc. Rev. 2013, 42, 8200–8219;
- 16cM. H. Koc, G. C. Ciftci, S. Baday, V. Castelletto, I. W. Hamley, M. O. Guler, Langmuir 2017, 33, 7947–7956.
- 17
- 17aY. Han, Y. Wang, Phys. Chem. Chem. Phys. 2011, 13, 1939–1956;
- 17bR. Zana, Adv. Colloid Interface Sci. 2002, 97, 205–253;
- 17cY. J. Li, X. Y. Wang, Y. L. Wang, J. Phys. Chem. B 2006, 110, 8499–8505;
- 17dD. Yu, X. Huang, M. Deng, Y. Lin, L. Jiang, J. Huang, Y. Wang, J. Phys. Chem. B 2010, 114, 14955–14964.
- 18
- 18aP. Zhang, J. Ma, X. Kang, H. Liu, C. Chen, Z. Zhang, J. Zhang, B. Han, Chem. Commun. 2017, 53, 2162–2165;
- 18bA. Brizard, C. Aime, T. Labrot, I. Huc, D. Berthier, F. Artzner, B. Desbat, R. Oda, J. Am. Chem. Soc. 2007, 129, 3754–3762;
- 18cR. Oda, I. Huc, M. Schmutz, S. J. Candau, F. C. MacKintosh, Nature 1999, 399, 566–569.
- 19L. Zhou, J. Yue, Y. Fan, Y. Wang, Langmuir 2018, 34, 12924–12933.
- 20H.-s. Peng, J. A. Stolwijk, L.-N. Sun, J. Wegener, O. S. Wolfbeis, Angew. Chem. Int. Ed. 2010, 49, 4246–4249; Angew. Chem. 2010, 122, 4342–4345.
- 21K. Liu, X. Qiao, C. Huang, X. Li, Z. Xue, T. Wang, Angew. Chem. Int. Ed. 2021, 60, 14365–14369; Angew. Chem. 2021, 133, 14486–14490.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.