Formation of supramolecular isomers; poly[2]rotaxane and supramolecular assembly

Miyawaki, Atsuhisa; Miyauchi, Masahiko; Takashima, Yoshinori; Yamaguchi, Hiroyasu; Harada, Akira

doi:10.1039/b713588b

Cited by 39 publications

(31 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Synthetic functional host molecules, such as calixarenes (CXs), [1][2][3][4][5][6] cyclodextrins (CDs), [7][8][9][10][11] and viologen dications (VGD), [12][13][14][15] that are capable of binding target molecules, have attracted considerable research interest in relation to SERS. The affinity of a metal surface can be increased by its functionalization with host molecules or cavitands.…”

Section: Introductionmentioning

confidence: 99%

Ultrasensitive SERS Detection of TNT by Imprinting Molecular Recognition Using a New Type of Stable Substrate

Yang

Chen

et al. 2010

Chemistry A European J

158

View full text Add to dashboard Cite

We report herein a method for the ultra-trace detection of TNT on p-aminothiophenol-functionalized silver nanoparticles coated on silver molybdate nanowires based on surface-enhanced Raman scattering (SERS). The method relies on π-donor-acceptor interactions between the π-acceptor TNT and the π-donor p,p'-dimercaptoazobenzene (DMAB), with the latter serving to cross-link the silver nanoparticles deposited on the silver molybdate nanowires. This system presents optimal imprint molecule contours, with the DMAB forming imprint molecule sites that constitute SERS "hot spots". Anchoring of the TNT analyte at these sites leads to a pronounced intensification of its Raman emission. We demonstrate that TNT concentrations as low as 10(-12) M can be accurately detected using the described SERS assay. Most impressively, acting as a new type of SERS substrate, the silver/silver molybdate nanowires complex can yield new silver nanoparticles during the detection process, which makes the Raman signals very stable. A detailed mechanism for the observed SERS intensity change is discussed. Our experiments show that TNT can be detected quickly and accurately with ultra-high sensitivity, selectivity, reusability, and stability. The results reported herein may not only lead to many applications in SERS techniques, but might also form the basis of a new concept for a molecular imprinting strategy.

show abstract

Section: Introductionmentioning

confidence: 99%

Ultrasensitive SERS Detection of TNT by Imprinting Molecular Recognition Using a New Type of Stable Substrate

Yang

Chen

et al. 2010

Chemistry A European J

158

View full text Add to dashboard Cite

show abstract

“…Poly [2]rotaxanes (daisy chain) are formed by 3-p-NH 2 CiNH-a-CD stabilized by bulky stoppers (TNBS and adamantanamide) at each end of the guest groups (Figure 2.9a). MALDI-TOF indicates that poly [2]rotaxane is about 13 units long [46]. 3-p-NH 2 CiNH-a-CD has been further modified with a tert-butoxycarbonyl (t-Boc) group at the end of the guest moiety to form more stable supramolecular polymers.…”

Section: Supramolecular Structures Formed By 3-modified A-cdsmentioning

confidence: 99%

Cyclodextrin‐Based Supramolecular Polymers

Harada

Takashima

2011

Supramolecular Polymer Chemistry

Self Cite

View full text Add to dashboard Cite

“…MALDI are R-cyano-4-hydroxycinnamic acid, 12 2,5-dihydroxybenzoic acid, 15 and sinapinic acid. 5 trans-3-Indoleacrylic acid, 17 2 0 ,4 0 ,6 0 -trihydroxyacetophenone, 9 2,5-dihydroxybenzoic acid, 10 and dithranol 17 were also successfully applied to detection of PPRs/PRs without CD.…”

Section: Articlementioning

confidence: 99%

Toward a More Accurate Structural Determination of High Molecular Weight Polyrotaxanes Based on Cyclodextrins by MALDI−TOF MS

2011

View full text Add to dashboard Cite

High molecular weight polyrotaxanes are usually characterized by nuclear magnetic resonance and size exclusion chromatography but rarely by mass spectrometry. This article reports effort to detect high molecular weight structures of cyclodextrin based polyrotaxanes (CD based PRs) by matrix-assisted laser desorption ionization mass spectrometry (MALDI−TOF MS). A particular attention was paid to verify the composition of the polyrotaxanes by determination of the number of macrocycles borne by the polyrotaxane and the polyrotaxanes synthetic route. Various matrices including crystalline or ionic liquid ones were screened to optimize the detection. Dimethylformamide as solvent widely used in supramolecular chemistry, but unusual in mass spectrometry, was successfully employed during all analyses. To prove the ability of the optimized MALDI−TOF MS conditions, three different polyrotaxane structures varying by polymer nature, i.e., poly(ethylene oxide) or polydimethylsiloxane and cyclodextrins type i.e. α or γ with or without modifications were evaluated. Finally, we have concluded that 1,1,3,3-tetramethylguanidinium salts of both 2-(4-hydroxyphenylazo)benzoic acid and 2′,4′,6′-trihydroxyacetophenone, are the most reliable and efficient matrices. These ones afforded the possibility to detect masses of 24804 and 26447 g·mol−1, corresponding to poly[17]- and poly[18]rotaxanes, respectively.

show abstract

Formation of supramolecular isomers; poly[2]rotaxane and supramolecular assembly

Abstract: Poly[2]rotaxane and supramolecular assembly have been prepared by modified cyclodextrins bearing an adamantyl group in an aqueous medium.

Cited by 39 publications

References 45 publications

Ultrasensitive SERS Detection of TNT by Imprinting Molecular Recognition Using a New Type of Stable Substrate

Ultrasensitive SERS Detection of TNT by Imprinting Molecular Recognition Using a New Type of Stable Substrate

Cyclodextrin‐Based Supramolecular Polymers

Toward a More Accurate Structural Determination of High Molecular Weight Polyrotaxanes Based on Cyclodextrins by MALDI−TOF MS

Contact Info

Product

Resources

About