Reversible dynamic optical sensing based on coumarin modified β-cyclodextrin for glutathione in living cells

Liu, Zhixue; Tian, Mengdi; Zhang, Heng; Liu, Yu

doi:10.1039/d2cc06512f

Cited by 14 publications

(3 citation statements)

References 36 publications

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“…The butyl-naphthalimide (NH) with flexible ethylenediamine link to 𝛽-CD usually forms a selfinclusion structure through supramolecular host-guest recognition (Scheme 1a). [36][37][38] However, since dimers or supramolecular polymers (SMPs) are possible for chromophore-𝛽-CD conjugates with a rigid link, [39,40] we perform 1 H NMR, GPC, and TOP-MS to identify the assemblies of N-CD (Figure S13, Supporting Information). First, concentration-dependent 1 H NMR results show no significant changes in proton signals on butyl chain, naphthalene ring, and 𝛽-CD with increasing N-CD concentration, suggesting no intermolecular associations.…”

Section: Resultsmentioning

confidence: 99%

Erasable, Rewritable, and Reprogrammable Dual Information Encryption Based on Photoluminescent Supramolecular Host–Guest Recognition and Hydrogel Shape Memory

Yang

Zheng

et al. 2023

Advanced Materials

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Information encryption technologies are very important for security, health, commodity, and communications, etc. Novel information encryption mechanisms and materials are desired to achieve multi‐mode and re‐programmable encryption. Here, we demonstrate a supramolecular strategy to achieve multi‐modal, erasable, reprogrammable, and reusable information encryption by reversibly modulating fluorescence. A butyl‐naphthalimide with flexible ethylenediamine functionalized β‐cyclodextrin (N‐CD) is utilized as fluorescent responsive ink for printing or patterning information on polymer brushes with dangling adamantane group grafted on responsive hydrogels. The photoluminescent naphthalimide moiety is bonded to β‐CD and entrapped in the cavity. Its fluorescence is highly weakened in β‐CD cavity and recovers after being expelled from the cavity by a competing guest molecule to emit bright green photoluminescence under UV. Experiments and theoretical calculations suggest π‐π stacking and ICT as the primary mechanism for the naphthalimides assembly and fluorescence, which can be quenched through insertion of conjugated molecules and recover by removing the insert. Such reversible quenching and recovering are used to achieve repeated writing, erasing, and re‐writing of information. We further combine supramolecular recognition and hydrogel shape memory to achieve reversible dual‐encryption. This study provides a novel strategy to develop smart materials with improved information security for broad applications.This article is protected by copyright. All rights reserved

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Section: Resultsmentioning

confidence: 99%

Erasable, Rewritable, and Reprogrammable Dual Information Encryption Based on Photoluminescent Supramolecular Host–Guest Recognition and Hydrogel Shape Memory

Yang

Zheng

et al. 2023

Advanced Materials

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“…[21] Therefore, multiple charged cyclodextrins, which possess positively or negatively charged units on the primary and secondary side, were the best second candidate. [22] Meanwhile, the main component in cyclodextrins are D-glucose units rather than aromatic ring, [23] so the quenching phenomenon of fluorophore can also be avoided. Based on the successfully construction of the multilevel supramolecular assemblies through various noncovalent interactions, the modulation of topological morphology and multicolor luminescence behaviors will be realized.…”

Section: Introductionmentioning

confidence: 99%

Configurationally Confined Multilevel Supramolecular Assemblies for Modulating Multicolor Luminescence

Tian

Wang

Yuan

et al. 2023

Adv Funct Materials

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Herein, multilevel supramolecular assemblies are reported based on sulfobutylether‐β‐cyclodextrin (SBE‐βCD) and cucurbit[8]uril (CB[8]), which can control the topological morphology from nanoparticles to nanosheets and modulate the multicolor luminescence. Benefiting from the large cavity of CB[8] and its strong binding affinity with positively charged tetraphenylethylene pyridinium (TPE‐Py), a 1:2 stoichiometric supramolecular assembly is formed through host–guest interactions with binding constants of 2.95 × 1011 M−2 and fluorescence bathochromic shift about 35 nm due to the macrocyclic confinement effect, thereby endowing the fluorescence enhancement about 20 times when further assembled with negatively charged SBE‐βCD to form nanosheets through electrostatic interactions. In contrast, the direct assembly of TPE‐Py and SBE‐βCD can form nanoparticles through electrostatic interactions, showing only tenfold enhancement and no bathochromic shift due to the lack of macrocyclic confinement effect. After doping the near‐infrared dye acceptor sulfonated aluminum phthalocyanine (AlPcS4), the nanosheets structure exhibits a higher energy transfer efficiency of about 75% and a larger antenna effect of 29.3 than that of nanoparticles. The multilevel supramolecular assemblies can be used in multicolor luminescence information storage and multiple logical gate systems, providing an efficient approach for configurationally confined topological morphology regulation and luminescent materials.

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“…9 These molecules have a large volume that enables them to accommodate various guest molecules via inclusion complexation. Native CDs 10,11 are semi-natural cyclic oligosaccharides with six to eight glucose units in a conical hollow cylindrical structure called α-, β-, and γ-CDs. Among them, β-CD 12 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in β-cyclodextrin-based materials for chiral recognition

Guo

Hou

et al. 2023

Chem. Commun.

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Reversible dynamic optical sensing based on coumarin modified β-cyclodextrin for glutathione in living cells

Abstract: Coumarin acts as an optical probe was modified on ethylenediamine β-cyclodextrin, not only enhanced molecular binding affinity to glutathione through reversible Michael addition, showing 113 times more affinity than that...

Cited by 14 publications

References 36 publications

Erasable, Rewritable, and Reprogrammable Dual Information Encryption Based on Photoluminescent Supramolecular Host–Guest Recognition and Hydrogel Shape Memory

Erasable, Rewritable, and Reprogrammable Dual Information Encryption Based on Photoluminescent Supramolecular Host–Guest Recognition and Hydrogel Shape Memory

Configurationally Confined Multilevel Supramolecular Assemblies for Modulating Multicolor Luminescence

Recent advances in β-cyclodextrin-based materials for chiral recognition

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