Complex Formation of Cyclodextrins with Various Thiophenes and their Polymerization in Water: Preparation of Poly-pseudo-rotaxanes containing Poly(thiophene)s

Takashima, Yoshinori; Sakamoto, Kazuya; Oizumi, Yoshifumi; Yamaguchi, Hiroyasu; Kamitori, Shigehiro; Harada, Akira

doi:10.1007/s10847-006-9059-4

Cited by 22 publications

(24 citation statements)

References 26 publications

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“…The formation of main‐chain polypseudorotaxanes was further studied using CDs and a variety of polymers. Pseudorotaxanes are formed from a number of combinations of CDs and polymers, including not only water‐soluble polymers but also polymers insoluble in water , . These observations indicate that main‐chain polypseudorotaxanes are formed universally by recognition by CDs of the cross‐sectional area of the polymer chain.…”

Section: Polyrotaxanes and Polypseudorotaxanesmentioning

confidence: 96%

Cyclodextrin‐Based Rotaxanes: from Rotaxanes to Polyrotaxanes and Further to Functional Materials

2019

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This minireview overviews rotaxanes and pseudorotaxanes containing cyclodextrins (CDs) as the rotor component. Since CDs interact with molecules, e.g., hydrophobic compounds of the size and shape matching their cavity, to form inclusion complexes in aqueous media, CDs are an important class of macrocyclic compounds as rotor components of rotaxanes and pseudorotaxanes. Research on CD‐based rotaxanes has begun with the synthesis of rotaxanes from low molecular weight axis molecules and then developed into the construction of molecular machines and polyrotaxanes. Recently, the research has further developed into macroscopic functional materials, e.g., slide‐ring gels, macromolecular assemblies, self‐healing materials, and soft actuators. In the present article, typical examples of CD‐based rotaxanes and pseudorotaxanes are described; synthesis of rotaxane and construction of molecular machine are described in Section 2, synthesis of polyrotaxanes is dealt with in Section 3, and development of macroscopic functional materials based on rotaxane structure is discussed in Section 4.

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Section: Polyrotaxanes and Polypseudorotaxanesmentioning

confidence: 96%

Cyclodextrin‐Based Rotaxanes: from Rotaxanes to Polyrotaxanes and Further to Functional Materials

2019

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“…Tables 6 and 7 summarize previous reports about polypseudorotaxanes with π-conjugated polymers (oligomers) such as poly(p-phenylene) (69-71), poly(fluorene) (71), poly(4,4 -diphenylenevinylene) (71), poly(phenylenevinylene) (72,73), polythiophene (PT) (74)(75)(76)(77)(78)(79), and polyaniline (80)(81)(82)(83)(84)(85)(86)(87). The inclusion complex between Hydroxypropyl (HP)-β-CD and 2thiophene (2T) gives polypseudorotaxane with PT, which can be prepared by electropolymerization in aqueous solutions (77).…”

Section: Complex Formation Between Cds and Ptsmentioning

confidence: 97%

“…The inclusion complex between Hydroxypropyl (HP)-β-CD and 2thiophene (2T) gives polypseudorotaxane with PT, which can be prepared by electropolymerization in aqueous solutions (77). The inclusion complexes, 2T ⊂ β-CD and 2T ⊂ Dimethyl (DM)-β-CD, are polymerized by the aqueous oxidative reaction to obtain polypseudorotaxanes (75,76).…”

Section: Complex Formation Between Cds and Ptsmentioning

confidence: 99%

Polyrotaxanes

Harada

Hashidzume

Yamaguchi

et al. 2012

Encyclopedia of Polymer Science and Technology

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A large number of examples of polyrotaxanes have been reported. These examples include various macrocycles, for example, crown ethers, cyclophanes, calyx[ n ]arenas, cyclodextrins (CDs), cucurbiturils, cyclobis(paraquat‐ p ‐phenylene), and pillararenes, and numerous types of axes depending on the macrocycles. Polyrotaxanes are categorized into two classes based on their structure: main‐chain polyrotaxanes and side‐chain polyrotaxanes. In the former, macrocyles include the polymer main chain, whereas side chains in the latter. This review shows typical examples of main‐chain and side‐chain polyrotaxanes, mainly focusing on CDs.

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“…The structure of the naringenin/DM-β-CD inclusion complex was solved by molecular replacement, using the atomic coordinates of the DM-β-CD macrocycle of the bithiophene/DM-β-CD complex [26]. The molecular replacement solution was obtained by a Patterson vector search and Fourier recycling using the DIRDIF99 package [27].…”

Section: Crystal Structure Determinationmentioning

confidence: 99%

Inclusion Complexes of Naringenin in Dimethylated and Permethylated β-Cyclodextrins: Crystal Structures and Molecular Dynamics Studies

2019

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The crystal structures of the inclusion complexes of naringenin in dimethylated and permethylated β-cyclodextrin (DM-β-CD and TM-β-CD) were determined and extensively analyzed. Naringenin is found with its 4-hydroxyphenyl residue fully immersed in the DM-β-CD cavity and its chromone group protruding from the narrow rim of the open-cone shaped host. The naringenin/DM-β-CD complex units are packed in a ‘herring bone’ fashion. In the case of naringenin/TM-β-CD, the complex units are arranged in a cage-type mode, the guest naringenin is partially encapsulated in the cavity of the closed-cone shaped host, with its chromone group laying equatorially and its 4-hydroxyphenyl protruding extensively from the wide rim of the host. Furthermore, the crystallographically-determined coordinates of both complexes were employed for Molecular Dynaimics simulations in explicit water solvent and in the absence of crystal contacts. The trajectories showed that naringenin rapidly penetrates the open narrow rim of DM-β-CD but not the closed narrow rim of TM-β-CD. Thus, in the latter case, the chromone group of naringenin is accommodated shallowly in the wide rim of the host, tethered via hydrogen bonds to the secondary methoxy groups of the host. Finally, a significantly higher binding affinity for naringenin in DM-β-CD than TM-β-CD was estimated by Molecular Mechanics/Generalized Born Surface Area calculations.

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Complex Formation of Cyclodextrins with Various Thiophenes and their Polymerization in Water: Preparation of Poly-pseudo-rotaxanes containing Poly(thiophene)s

Cited by 22 publications

References 26 publications

Cyclodextrin‐Based Rotaxanes: from Rotaxanes to Polyrotaxanes and Further to Functional Materials

Cyclodextrin‐Based Rotaxanes: from Rotaxanes to Polyrotaxanes and Further to Functional Materials

Polyrotaxanes

Inclusion Complexes of Naringenin in Dimethylated and Permethylated β-Cyclodextrins: Crystal Structures and Molecular Dynamics Studies

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