Reversible and contrasting changes of the cloud point temperature of pillar[5]arenes with one quinone unit and tri(ethylene oxide) chains induced by redox chemistry and host–guest complexation

Ogoshi, Tomoki; Akutsu, Tomohiro; Tamura, Yuko; Yamagishi, Toshio

doi:10.1039/c5cc01630d

Cited by 21 publications

(23 citation statements)

References 36 publications

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“…72 The cloud point of quinone-134 [5] in 2 mM aqueous solution was observed at 21°C, which was lower than that of the amphiphilic pillar [5]arene without the benzoquinone unit (41°C in 51 [5]). This difference in the cloud points was attributed to the benzoquinone unit being more hydrophobic than the tri(ethylene oxide)-modified unit.…”

Section: Application Of Pillar[n]arene-based Host−guest Systemsmentioning

confidence: 95%

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

2016

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In 2008, we reported a new class of pillar-shaped macrocyclic hosts, known as "pillar[n]arenes". Today, pillar[n]arenes are recognized as key players in supramolecular chemistry because of their facile synthesis, unique pillar shape, versatile functionality, interesting host-guest properties, and original supramolecular assembly characteristics, which have resulted in numerous electrochemical and biomedical material applications. In this Review, we have provided historical background to macrocyclic chemistry, followed by a detailed discussion of the fundamental properties of pillar[n]arenes, including their synthesis, structure, and host-guest properties. Furthermore, we have discussed the applications of pillar[n]arenes to materials science, as well as their applications in supramolecular chemistry, in terms of their fundamental properties. Finally, we have described the future perspectives of pillar[n]arene chemistry. We hope that this Review will provide a useful reference for researchers working in the field and inspire discoveries concerning pillar[n]arene chemistry.

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Section: Application Of Pillar[n]arene-based Host−guest Systemsmentioning

confidence: 95%

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

2016

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“…63 Other useful methods of producing water-soluble P[n]As are through modification of their rims with cationic moieties 64 and nonionic oligo(ethylene oxide) chains. 65 Water-soluble P[n]As have begun to play an important role in supramolecular theranostics nanosystems.…”

Section: P[n]mentioning

confidence: 99%

Turn-On Supramolecular Host-Guest Nanosystems as Theranostics for Cancer

Cheng

Zhang

Liu

et al. 2019

Chem

103

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Cancer is one of the world's most serious health challenges. Several problems and challenges still exist for cancer therapies especially because anti-cancer agents that are delivered to normal cells and tissues cause a number of severe side effects. In one general approach aimed at solving this problem, supramolecular systems, created by noncovalent interactions, have been designed and utilized for cancer-cell-targeted drug delivery. In addition, cancer-associated, turn-on supramolecular theranostic agents have received great attention in the biomedicine field because they can be selectively ''switched on'' in cancer cells. This attribute enables the avoidance of problems associated with cytotoxic effects on healthy cells and tissues. In this review, we summarize recent progress made in the design of turn-on supramolecular theranostic agents composed of host-guest nanosystems and their applications in biomedicine.

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“…Table 1 summarizes the partial oxidation processes of the pillar[5]arenes 1 a-1 d to the presently known pillar [5-m]arene[m]quinones 4-6, 8 and 9 (Figure 2). [5,[13][14][15][16][17][18][19][20][21][22][23] Certain molar ratios 1/oxidizing agent led to the formation of a preferred number m of quinone rings in the product. A column chromatography was conventionally used for the separation and purification of the products.…”

Section: Pillar[n-m]arene[m]quinonesmentioning

confidence: 99%

“…[30,31] The subsequent oxidation to pillararenequinones is preparatively less advisable and is limited to special cases such as 13 a. [26] The reverse process, the reduction of pillararenequinones to pillararenehydroquinones was practiced many times by applying NaBH 4 [14,17,20,21,23,32] , Na 2 S 2 O 4 [13,15,18,24,25,28] or Zn/AcOH [26] as reducing agents. The yields were very high, in many cases quantitative.…”

Section: Pillar[n-m]arene[m]quinonesmentioning

confidence: 99%

Pillarquinones and Pillararenequinones

Cao

Meier

2018

Israel Journal of Chemistry

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Pillar[n]quinones and pillar [n-m]arene [m]quinones are oxidation products of pillar[n]arenes. Their molecular structure resembles the parent compounds. However, their map of electron density is different. Each 1,4-benzoquinone ring, which replaces a 1,4-dialkoxy-substituted benzene ring decreases the electron density in the interior cavity and increases the electron density on the upper and lower rim of the pillar. The electron donor character is stepwise transformed to an electron acceptor status. This effect alters the complexation tendencies, which are the most interesting properties of these macrocyclic host systems. Figure 1. Pillar[n]arenes and pillar[5]quinone.Figure 2. Pillar[5-m]arene[m]quinones (m = 1-5).

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Reversible and contrasting changes of the cloud point temperature of pillar[5]arenes with one quinone unit and tri(ethylene oxide) chains induced by redox chemistry and host–guest complexation

Abstract: A new water-soluble redox-active pillar[5]arene was synthesized by incorporation of one benzoquinone unit. The pillar[5]arene showed redox-responsive reversible lower critical solution temperature changes in aqueous solution.

Cited by 21 publications

References 36 publications

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry

Turn-On Supramolecular Host-Guest Nanosystems as Theranostics for Cancer

Pillarquinones and Pillararenequinones

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