Tailoring pillararene-based receptors for specific metal ion binding: From recognition to supramolecular assembly

Fang, Yuyu; Deng, Yun; Dehaen, Wim

doi:10.1016/j.ccr.2020.213313

Cited by 65 publications

(34 citation statements)

References 186 publications

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“…To date, various classic fluorescence dyes, acting as signal reporters such as coumarins [ 35 ], 1,8-naphthalimides [ 36 , 37 ], rhodamines [ 38 ], difluoroboron dipyrromethenes (better known as BODIPY) [ 39 , 40 , 41 , 42 ], cyanine dyes [ 43 ], pyrene [ 44 , 45 , 46 ], AIE-active luminogens [ 47 , 48 , 49 ] and so on [ 50 , 51 , 52 ], have been widely developed to construct fluorescent chemosensors for broad and exciting applications. Recently, we have summarized small-molecule-based fluorescent probes for f-block metal ions [ 53 ] and pillararene-based receptors for binding of different metal ions [ 54 ] as well as fluorescent chemosensors and smart materials constructed from macrocyclic arenes that incorporate BODIPY [ 55 ]. Specifically, the reaction-based fluorescent probes (also known as chemodosimeters), whose recognition events involve irreversible chemical reactions as induced by a target analyte, have received great attention during the last decade as this promising and attractive strategy always offers high selectivity and sensitivity [ 56 , 57 , 58 , 59 ].…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Probes for Selective Recognition of Hypobromous Acid: Achievements and Future Perspectives

Fang

Dehaen

2021

Molecules

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Reactive oxygen species (ROS) have been implicated in numerous pathological processes and their homeostasis facilitates the dynamic balance of intracellular redox states. Among ROS, hypobromous acid (HOBr) has a high similarity to hypochlorous acid (HOCl) in both chemical and physical properties, whereas it has received relatively little attention. Meanwhile, selective recognition of endogenous HOBr suffers great challenges due to the fact that the concentration of this molecule is much lower than that of HOCl. Fluorescence-based detection systems have emerged as very important tools to monitor biomolecules in living cells and organisms owing to distinct advantages, particularly the temporal and spatial sampling for in vivo imaging applications. To date, the development of HOBr-specific fluorescent probes is still proceeding quite slowly, and the research related to this area has not been systematically summarized. In this review, we are the first to review the progress made so far in fluorescent probes for selective recognition and detection of HOBr. The molecular structures, sensing mechanisms, and their successful applications of these probes as bioimaging agents are discussed here in detail. Importantly, we hope this review will call for more attention to this rising field, and that this could stimulate new future achievements.

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Section: Introductionmentioning

confidence: 99%

Fluorescent Probes for Selective Recognition of Hypobromous Acid: Achievements and Future Perspectives

Fang

Dehaen

2021

Molecules

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“…[14][15][16][17][18] Pillar[n]arenes and its derivatives are well-known for their applications in the field of chemosensors, [19][20][21] supramolecular polymers, [22] molecular recognition, [23][24][25][26] transmembrane channels, [27] biofilm inhibition, [28][29] drug delivery systems, [30][31] biomedical, [32][33][34] catalysis, [35] porous materials, [36] organogels, [37] and nanotubes. [38] Several researchers have reviewed the excellent properties of pillar [n]arenes and its derivatives in recent years and these include, i) its synthesis, fundamental properties, host-guest recognition, material chemistry applications, [39][40][41][42][43][44][45][46][47][48] (ii) metal ion binding, [49] (iii) water solublility, [50][51] (iv) molecular recognition and selfassembly, [52][53][54] (vi) chemosensing properties, [55] (vii) metal ion separation, [56] (viii) gelation properties, …”

Section: Introductionmentioning

confidence: 99%

Pillar[n]arene Derivatives as Sensors for Amino Acids

Joseph

2021

ChemistrySelect

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Owing to the involvement in various biological processes, developing sensors for the detection of amino acids is an important area of research. Pillar [n]arenes are elegant macrocyclic systems that have been used as potential host systems for various applications including the sensing of ions and molecules. Since its inclusion in 2008, pillar [n]arenes and its derivatives have received much attention among the researchers, and these molecular systems are used as excellent host systems for the formation of inclusion complexes with various guest molecules which have relevance both in chemistry and biology. Herein, we highlight the recent developments on the sensing of amino acids by pillar[n]arene derivatives. The majority of the sensors we discussed here detect amino acids by fluorescence techniques and their sensing was further supported by various other spectroscopic methods. In some cases sensing was achieved visually by the change in colour of the host system upon interaction with the amino acids.

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“…Supramolecular host-guest chemistry has attracted significant interest in the fields of material science, molecular recognition, gas storage, drug delivery, and biomedical engineering. [1][2][3][4][5][6][7][8] At present, hosts with an intrinsic cavity, capsule or cage-type structure have been constructed based on various noncovalent interactions to recognize or capture guest molecules among various other applications. [9][10][11] Such hosts include metal-organic, covalent-organic, hydrogen-bonded organic, and halogenbonded organic frameworks, as well as porous organic polymers and inclusion crystals.…”

Section: Introductionmentioning

confidence: 99%

Ternary Cocrystals with Large Soft Cavities: A 1,4‐diiodotetrafluorobenzene (DITFB)⋅4‐Biphenylpyridine N‐oxide (BPNO) Host Assembled by Inclusion of Planar Aromatic Guests

et al. 2021

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A large soft-cavity host composed of 1,4-diiodotetrafluorobenzene (DITFB) and 4-biphenylpyridine N-oxide (BPNO) is assembled under the mediation of a planar aromatic guest molecule (pyrene or perylene) through CÀ I••• À OÀ N + halogen bonds and π-hole•••π bonds. Single-crystal X-ray diffraction reveals that guest molecules can be completely encapsulated in the four-layer host cavity to assemble ternary host-guest cocrystals; namely, Pyr@DITFB • BPNO and Per@DITFB • BPNO. The luminescence of these ternary cocrystals originates from their discrete guest molecules, which exhibit pure-blue and yellow emissions, respectively, that are localized at 425 nm and in the range of 485 to 578 nm, respectively. In addition, the contribution of different fragments to the stabilization of the crystal structure is estimated by computational chemistry. These cocrystals have significant potential for use in optical applications or materials, such as photonics or organic light-emitting diodes, respectively, that require to avoid the aggregation between luminophores.

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Tailoring pillararene-based receptors for specific metal ion binding: From recognition to supramolecular assembly

Cited by 65 publications

References 186 publications

Fluorescent Probes for Selective Recognition of Hypobromous Acid: Achievements and Future Perspectives

Fluorescent Probes for Selective Recognition of Hypobromous Acid: Achievements and Future Perspectives

Pillar[n]arene Derivatives as Sensors for Amino Acids

Ternary Cocrystals with Large Soft Cavities: A 1,4‐diiodotetrafluorobenzene (DITFB)⋅4‐Biphenylpyridine N‐oxide (BPNO) Host Assembled by Inclusion of Planar Aromatic Guests

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