A twin-axial pseudorotaxane for phosphorescence cell imaging

Ma, Xin-Kun; Zhang, Ying‐Ming; Yu, Qilin; Zhang, Haoyang; Zhang, Zhiyuan; Liu, Yu

doi:10.1039/d0cc06717b

Cited by 28 publications

(22 citation statements)

References 23 publications

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“…Diethanolamine-modified phenylpyridine formed twin-axial pseudorotax-ane after binding with CB [8]. 37 Because of the "head-to-tail" binding form and hydrogen bond between diethanol amine and CB [8], the distance between Br and OC was drawn close, and this promoted the formation of the halogen bond (Figure 5a). Furthermore, the cooperative effect of the host's rigid cavity and blocking of diethanol amine further protected the assembly from water.…”

Section: Phosphorescence In Aqueous Solutionmentioning

confidence: 99%

“…In addition to constructing nanoparticles, supramolecular assembly was utilized to enhance the intermolecular interaction between phosphors and then facilitate phosphorescence. Diethanolamine-modified phenylpyridine formed twin-axial pseudorotaxane after binding with CB[8] . Because of the “head-to-tail” binding form and hydrogen bond between diethanol amine and CB[8], the distance between Br and OC was drawn close, and this promoted the formation of the halogen bond (Figure a).…”

Section: Macrocycles Enhance Guest’s Phosphorescencementioning

confidence: 99%

Section: Macrocycles Enhance Guest’s Phosphorescencementioning

confidence: 99%

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Supramolecular Purely Organic Room-Temperature Phosphorescence

2021

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Conspectus In recent years, purely organic room-temperature phosphorescence (RTP) has aroused wide concern and promotes the development of the supramolecular phosphorescence. Different from organic crystallization, polymerization, or matrix rigidification, supramolecular strategy mainly takes advantage of the synergy between supramolecular co-assembly and strong binding by macrocyclic host compounds (cucurbit[n]urils, cyclodextrins, etc.) to overcome deficiencies such as poor processability and water solubility and improves RTP materials’ quantum efficiency and lifetime in the solid state or in an aqueous solution. Meanwhile, it expands application, especially in aqueous solution, in cell imaging. Therefore, supramolecular phosphorescence will become a new growth point and will have broad application prospects in chemistry, biology, and material science. This Account focuses on the uniquely synergetic advantages of co-assembly and host–guest interaction from macrocyclic hosts for enhancing RTP. This Account starts with a brief introduction of the recent development of organic RTP materials as well as the host–guest interaction and co-assembly. Then, we introduce a supramolecular solid-state RTP strategy involving an ultrahigh phosphorescent quantum yield via the tight encapsulation of macrocyclic host cucurbit[6]uril, an ultralong lifetime via changing the substituents of phosphors, and long-lived and bright RTP by the synergy of host–guest interaction and polymerization. Meanwhile, the applications of solid-state RTP materials for anti-counterfeiting and data encryption are presented. The third part will be the water-phase supramolecular phosphorescence systems constructed by water-soluble macrocyclic host cucurbit[8]uril. Host–guest interaction and polymerization worked together toward efficient phosphorescence in aqueous solution, and the multi-stage assembly promoted phosphorescent applications such as cell targeted imaging and energy transfer. A humidity sensor and data encryption by the conversion of supramolecular hydrogels and xerogels are also involved. In the summary section, we present perspectives and possible research directions for supramolecular phosphorescence. Furthermore, on the basis of previous research, we would like to conclude and propose the developing concept of “macrocycles enhance guest’s phosphorescence”, and this concept not only means that the macrocyclic host limits the movement of the guest compound or promotes interactions between guest compounds but also involves the synergetic enhancement centered on macrocyclic compounds via multi-stage supramolecular assembly which further improves the efficiency of RTP, water solubility, and biocompatibility. And we believe that this concept will be able, together with theory of “assembly-induced emission” and “aggregation-induced emission”, to accelerate the development of purely organic RTP materials.

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Section: Phosphorescence In Aqueous Solutionmentioning

confidence: 99%

Section: Macrocycles Enhance Guest’s Phosphorescencementioning

confidence: 99%

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Supramolecular Purely Organic Room-Temperature Phosphorescence

2021

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“…50,51 Based on the above advantages, many efforts have contributed to the application of supramolecular macrocycles in purely organic RTP systems. 52–54 Tian and co-workers reported an approach to achieve amorphous purely organic RTP small molecules by modifying different phosphors onto β-cyclodextrin, which could suppress the non-radiative relaxation via intermolecular hydrogen bonding. 41 Recently, we reported that by modifying bromophenylpyridinium on hyaluronic acid and co-assembling with cucurbit[8]uril ( CB[8] ), a type of macrocycle formed by the polymerization of glycoluril and formaldehyde, 55,56 the resultant supramolecular assembly exhibited good RTP behavior in aqueous solution, which was successfully applied to mitochondrial-targeted imaging of cancer cells.…”

Section: Introductionmentioning

confidence: 99%

A tunable phosphorescence supramolecular switch by an anthracene photoreaction in aqueous solution

Liu

Chen

et al. 2022

J. Mater. Chem. C

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“…[ 4 ] Recently, we reported cucurbit[n]uril‐mediated ( n = 6–8) supramolecular phosphorescence assembly with long lifetime or high phosphorescence quantum yield. [ 5–8 ] However, controllable phosphorescence material remains a formidable challenge. It is well‐known that diarylethene derivatives could reversibly convert between two thermal stable isomers upon light irradiation.…”

Section: Introductionmentioning

confidence: 99%

Highly Reversible Supramolecular Light Switch for NIR Phosphorescence Resonance Energy Transfer

Wang

Guo

et al. 2021

Advanced Science

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Although purely organic room‐temperature phosphorescence (RTP) has drawn widespread attention in recent years, regulatable phosphorescence resonance energy transfer (PRET) supramolecular switch is still rare. Herein, single molecular dual‐fold supramolecular light switches, which are constructed by phenylpyridinium salts modified diarylethene derivatives (DTE‐Cn, n = 3, 5) and cucurbit[8]uril (CB[8]) are reported. Significantly, biaxial [3]pseudorotaxane displayed efficiently reversible RTP after binding with CB[8] and the phosphorescence quenching efficiency is calculated up to be 99%. Furthermore, the binary supramolecular assembly can coassemble with Cy5 to form ternary supramolecular assembly showing efficiently PRET, which is successfully applied in switchable near infrared (NIR) mitochondria‐targeted cell imaging and photocontrolled data encryption. This supramolecular strategy involving energy transfer provides a convenient approach for phosphorescent application in biology and material fields.

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A twin-axial pseudorotaxane for phosphorescence cell imaging

Abstract: A twin-axial pseudorotaxane is constructed using a phenylpyridine salt with diethanolamine (DA-PY) and cucurbit[8]uril (CB[8]), and it not only displays phosphorescence in aqueous solution but it can also be used for targeted cell-imaging.

Cited by 28 publications

References 23 publications

Supramolecular Purely Organic Room-Temperature Phosphorescence

Supramolecular Purely Organic Room-Temperature Phosphorescence

A tunable phosphorescence supramolecular switch by an anthracene photoreaction in aqueous solution

Highly Reversible Supramolecular Light Switch for NIR Phosphorescence Resonance Energy Transfer

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