一种基于萘基苯基丙烯腈的新型水相人工光捕获体系
A Novel Naphthalenyl-Phenyl-Acrylonitrile-Based Aqueous Artificial Light-Harvesting System
摘要: 本文以水溶性柱[6]芳烃(P[6]A)作为主体分子,萘基苯基丙烯腈衍生物(NPA)作为客体分子,两者在水中通过主–客体相互作用形成两亲性复合物,并进一步自组装成纳米颗粒(P[6]A-NPA)。该纳米颗粒可以对荧光染料尼罗红(NiR)进行包载,成功构筑了一种新型水相人工光捕获体系(P[6]A-NPA-NiR)。值得注意的是,当P[6]A-NPA与NiR的摩尔比达到100:1时,该体系的能量转移效率和天线效应分别达到了55%和14.0,为水相超分子人工光捕获领域的研究提供了新思路。
Abstract: A water-soluble pillar[6]arene (P[6]A) was used as host molecule and a naphthalenyl-phenyl-acrylonitrile-based derivative (NPA) was used as guest molecule. The amphiphilic complex of P[6]A-NPA was formed through host-guest interactions in water and further self-assembled into P[6]A-NPA nanoparticles. Moreover, the above nanoparticles can encapsulate the fluorescent dye Nile Red (NiR) and construct a novel aqueous artificial light-harvesting system (P[6]A-NPA-NiR). Notably, when the molar ratio of NPA and NiR reaches 100:1, the energy transfer efficiency and antenna effect of the system reach 55% and 14.0, providing new ideas in the field of aqueous supramolecular artificial light-harvesting systems.
文章引用:李梦行, 冯晋, 李家吉, 朱金丽, 汤艳峰, 孙广平. 一种基于萘基苯基丙烯腈的新型水相人工光捕获体系[J]. 有机化学研究, 2024, 12(3): 439-445. https://doi.org/10.12677/jocr.2024.123041

参考文献

[1] Meng, L., Li, D., Xiong, S., Hu, X., Wang, L. and Li, G. (2015) Fret-Capable Supramolecular Polymers Based on a Bodipy-Bridged Pillar[5]arene Dimer with BODIPY Guests for Mimicking the Light-Harvesting System of Natural Photosynthesis. Chemical Communications, 51, 4643-4646. [Google Scholar] [CrossRef] [PubMed]
[2] Chen, X., Chen, X., Hou, X., Zhang, S., Chen, D. and Li, Q. (2023) Self-Assembled Supramolecular Artificial Light-Harvesting Nanosystems: Construction, Modulation, and Applications. Nanoscale Advances, 5, 1830-1852. [Google Scholar] [CrossRef] [PubMed]
[3] Zong, H., Wang, X., Mu, X., Wang, J. and Sun, M. (2019) Plasmon-Enhanced Fluorescence Resonance Energy Transfer. The Chemical Record, 19, 818-842. [Google Scholar] [CrossRef] [PubMed]
[4] Wang, X., Lou, X., Lu, T., Wang, C., Tang, J., Liu, F., et al. (2021) Supramolecular Engineering of Efficient Artificial Light-Harvesting Systems from Cyanovinylene Chromophores and Pillar[5]arene-Based Polymer Hosts. ACS Applied Materials & Interfaces, 13, 4593-4604. [Google Scholar] [CrossRef] [PubMed]
[5] Duan, H., Li, Y., Li, Q., Wang, P., Liu, X., Cheng, L., et al. (2020) Host-Guest Recognition and Fluorescence of a Tetraphenylethene-Based Octacationic Cage. Angewandte Chemie International Edition, 59, 10101-10110. [Google Scholar] [CrossRef] [PubMed]
[6] Hao, M., Sun, G., Zuo, M., Xu, Z., Chen, Y., Hu, X., et al. (2019) A Supramolecular Artificial Light-Harvesting System with Two-Step Sequential Energy Transfer for Photochemical Catalysis. Angewandte Chemie, 132, 10181-10186. [Google Scholar] [CrossRef
[7] Geng, W., Liu, Y., Wang, Y., Xu, Z., Zheng, Z., Yang, C., et al. (2017) A Self-Assembled White-Light-Emitting System in Aqueous Medium Based on a Macrocyclic Amphiphile. Chemical Communications, 53, 392-395. [Google Scholar] [CrossRef] [PubMed]
[8] Liu, Z., Sun, X., Dai, X., Li, J., Li, P. and Liu, Y. (2021) Sulfonatocalix[4]arene-Based Light-Harvesting Amphiphilic Supramolecular Assemblies for Sensing Sulfites in Cells. Journal of Materials Chemistry C, 9, 1958-1965. [Google Scholar] [CrossRef
[9] Sun, G., Cai, L., Zhang, Y., Hu, Y., Zhu, J., Sun, T., et al. (2022) Salicylideneaniline-Based Aqueous Supramolecular Artificial Light-Harvesting Platforms with Biocompatibility. Dyes and Pigments, 205, Article 110577. [Google Scholar] [CrossRef
[10] Sun, G., Cai, L., Cui, H., Hu, Y., Wang, J., Wang, M., et al. (2022) Naphthalenyl-Phenylacrylonitrile-Based Supramolecular Aqueous Artificial Light-Harvesting System for Photochemical Catalysis. Dyes and Pigments, 201, Article 110257. [Google Scholar] [CrossRef
[11] Yu, G., Han, C., Zhang, Z., Chen, J., Yan, X., Zheng, B., et al. (2012) Pillar[6]arene-Based Photoresponsive Host-Guest Complexation. Journal of the American Chemical Society, 134, 8711-8717. [Google Scholar] [CrossRef] [PubMed]
[12] Duan, Q., Cao, Y., Li, Y., Hu, X., Xiao, T., Lin, C., et al. (2013) pH-Responsive Supramolecular Vesicles Based on Water-Soluble Pillar[6]arene and Ferrocene Derivative for Drug Delivery. Journal of the American Chemical Society, 135, 10542-10549. [Google Scholar] [CrossRef] [PubMed]
[13] Wu, Z., Zhang, Q., Chen, D. and Xiao, T. (2024) Artificial Light-Harvesting Nanoparticles Based on a Tripodal Fluorescence Sensor Mediated by Multiple Luminescence Mechanisms. Sensors & Diagnostics, 3, 295-300. [Google Scholar] [CrossRef
[14] Sun, G., Li, M., Cai, L., Wang, D., Cui, Y., Hu, Y., et al. (2023) Water-Soluble Phosphate-Pillar[5]arene (WPP5)-Based Artificial Light-Harvesting System for Photocatalytic Cross-Coupling Dehydrogenation. Journal of Colloid and Interface Science, 641, 803-811. [Google Scholar] [CrossRef] [PubMed]
[15] Li, X., Zhang, Q., Dang, X., Cui, F., Li, Z., Sun, X., et al. (2024) Construction of a Supramolecular Light-Harvesting System Based on Pillar[5]arene-Mediated Nanoparticles in Water. Energy Advances, 3, 1672-1677. [Google Scholar] [CrossRef