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Supramolecular assembly-enhanced chiroptical properties of pyrene-modified cyclodextrins
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Yu-Hui Zhanga, Yong Chenb, *
Chinese Chemical Letters | 2023, 34(3) : 107836
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Chinese Chemical Letters | 2023, 34(3): 107836
• Editorial •
Supramolecular assembly-enhanced chiroptical properties of pyrene-modified cyclodextrins
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Yu-Hui Zhanga, Yong Chenb, *
Affiliations
  • a College of Science, Inner Mongolia Agricultural University, Hohhot 010018, China
  • b College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
Published: 2023-03-15 doi: 10.1016/j.cclet.2022.107836
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Yu-Hui Zhang, Yong Chen. Supramolecular assembly-enhanced chiroptical properties of pyrene-modified cyclodextrins[J]. Chinese Chemical Letters, 2023 , 34 (3) : 107836 - . DOI: 10.1016/j.cclet.2022.107836
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Manipulating the chiroptical activities of chiral chromophores is helpful to expand the potential applications of circularly polarized luminescence (CPL) materials in the fields of chiral sensing, optical displays, biological probe, information storage and so on [1]. In recent years, macrocycles-based supramolecular systems have been continually and extensively applied in the fields of biomedicine, catalysis, optical and electronic materials [2,3]. In particular, supramolecular self-assembly, as an effective strategy to improve chiroptical activities, has attracted great attention [4]. However, the dynamic non-covalent interactions of supramolecular assemblies still make it challenging to restrict the chiral arrangement of chromophores strictly.
Recently, Yang and coworkers from Sichuan University reported a supramolecular strategy through a combination of host–guest complexation and supramolecular aggregation to obtain significant chiroptical properties [5]. They synthesized pyrene di-substituted γ-cyclodextrin (γ-CD) derivates, which self-assembled to supramolecular polymers in an aqueous solution with the pyrene moieties interpenetrating into γ-CD cavities. Subsequently, the self-assembled polymers further aggregated into nanostrips through the periphery of γ-CD (Figs. 1 and 2).
The host-guest complexation of γ-CD with pyrene gives rise to J-type stacking of pyrenes accompanied by apparent excimer fluorescence and the further aggregation restricts pyrene into a rigid chiral environment, thus exhibiting excellent chiral spectral properties. The gabs and glum values are up to 4.3 × 10−2 and 5.3 × 10−2, which surpassed the current record of chiral pyrene derivatives obtained in supramolecular aggregates. Due to the protective effect of cavity encapsulation and aggregation against the solvent collision, the fluorescence quantum efficiency Φf is up to 64.1% (Table 1). Moreover, temperature, pH and competitive guest can significantly affect the aggregation and manipulate the chiroptical properties (Fig. 2).
In addition, they used a newly proposed parameter BiCPL = BCPL/n to evaluate the chiral emission performance, where BCPL is the CPL brightness and n is the number of chromophore units in the molecule. Because of the high Φf and glum, the BCPL and BiCPL of this pyrene di-substituted γ-CD supramolecular system are 338.6 and 169.3 (mol/L)−1 cm−1, respectively, in which the BiCPL value is the highest one obtained with excimer fluorescence (Table 1).
In summary, Yang and coworkers have developed a supramolecular strategy based on pyrene-modified cyclodextrin by synergistic host-guest complexation-induced aggregation, which effectively confines the two pyrene units to a relatively rigid chiral environment, thus achieving significant enhancement of chiral optical activity. We believed that this strategy could be applied to other macrocyclic compounds, such as cucurbiturils, pillararenes, thus providing us with a novel toolbox to regulate the arrangement of chiral chromophores and enhance the CPL signals, meanwhile which could also be further modulated by temperature, light, pH and solvent change (Fig. 3). To be envisaged, this new strategy will play a more and more important role in the research and development of CPL field.
References
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[1]
M. Li, M.Y. Wang, Y.F. Wang, et al., Angew. Chem. Int. Ed. 60 (2021) 20728–20733.
[2]
Y. Zhang, L. Wang, J. Wang, et al., Chin. Chem. Lett. 32 (2021) 1902–1906.
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X.Y. Dai, Y.Y. Hu, Y. Sun, et al., Adv. Sci. 9 (2022) 2200524.
[4]
S. Zheng, J. Han, X. Jin, et al., Angew. Chem. Int. Ed. 60 (2021) 22711–22716.
[5]
C. Tu, W. Wu, W. Liang, et al., Angew. Chem. Int. Ed. 61 (2022) e202203541.
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Year 2023 volume 34 Issue 3
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Article Info
doi: 10.1016/j.cclet.2022.107836
  • Receive Date：2022-08-27
  • Online Date：2025-11-21
  • Published：2023-03-15
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  • Received：2022-08-27
  • Revised：2022-09-08
  • Accepted：2022-09-15
Affiliations
    a College of Science, Inner Mongolia Agricultural University, Hohhot 010018, China
    b College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
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表12种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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