A Pseudorotaxane on Gold: Formation of Self‐Assembled Monolayers, Reversible Dethreading and Rethreading of the Ring, and Ion‐Gating Behavior

Kim, Kyungpil; Jeon, Woo Sung; Kang, Jin-Koo; Lee, Jae Woo; Jon, Sang Yong; Kim, Taisun; Kim, Kimoon

doi:10.1002/ange.200250692

Cited by 50 publications

(30 citation statements)

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“…Kim and co-workers have reported the functionalization of a gold surface with the pseudorotaxane CB [6]·41. [154] Surface plasmon resonance (SPR) studies have shown that SAMs comprising CB [6]·41 undergo reversible dethreading and rethreading of the CB [6] beads upon treatment with 0.1m NaOH followed by CB [6]. Cyclic voltametry measurements indicate that the SAM formed by pseudorotaxane CB [6]·41 constitutes an effective barrier to redox processes involving [Fe(CN) 6 ] 3À : a quasireversible redox wave is observed after dethreading.…”

Section: Catalysismentioning

confidence: 97%

The Cucurbit[n]uril Family

et al. 2005

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In 1981, the macrocyclic methylene-bridged glycoluril hexamer (CB[6]) was dubbed "cucurbituril" by Mock and co-workers because of its resemblance to the most prominent member of the cucurbitaceae family of plants--the pumpkin. In the intervening years, the fundamental binding properties of CB[6]-high affinity, highly selective, and constrictive binding interactions--have been delineated by the pioneering work of the research groups of Mock, Kim, and Buschmann, and has led to their applications in waste-water remediation, as artificial enzymes, and as molecular switches. More recently, the cucurbit[n]uril family has grown to include homologues (CB[5]-CB[10]), derivatives, congeners, and analogues whose sizes span and exceed the range available with the alpha-, beta-, and gamma-cyclodextrins. Their shapes, solubility, and chemical functionality may now be tailored by synthetic chemistry to play a central role in molecular recognition, self-assembly, and nanotechnology. This Review focuses on the synthesis, recognition properties, and applications of these unique macrocycles.

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Section: Catalysismentioning

confidence: 97%

The Cucurbit[n]uril Family

et al. 2005

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“…Recent researches in the development of bioactive SAMs have tried to tackle the challenge of designing dynamic SAMs that could undergo on demand surface reactions under external stimuli. 3b, 11 Such smart surfaces provide unique switchable monolayers whose surface activities can be turned on only when needed. These smart surfaces may enable new applications in fields like controlled ligand immobilization, cell adhesion, and biochemical sensors.…”

Section: ■ Introductionmentioning

confidence: 99%

An Electrochemically Switched Smart Surface for Peptide Immobilization and Conformation Control

Sun

Shen

et al. 2014

J. Am. Chem. Soc.

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We report an electrochemically switched smart surface for controlled peptide immobilization and conformation control. This dynamic surface is based on self-assembled monolayers (SAMs) containing surface-bound trimethoxybenzene moieties, which can undergo electrochemically modulated surface activation to be stepwisely converted to two catechol derivatives. This new smart surface can be used to realize stepwise immobilization of a peptide, and more importantly, to control peptide conformation on a surface. We demonstrate herein that with one electrochemical activation step, a linear peptide containing an RGD sequence can be attached onto the SAMs. With the subsequence activation step, the attached linear RGD peptide can be converted into cyclic conformation. The SAMs bounded with linear and cyclic RGD exhibit different adhesion behaviors to fibroblasts cells. The reaction procedure can be well-monitored by cyclic voltammetry (CV), electrochemical surface enhanced Raman microscopy (EC-SERS), and X-ray photoelectron spectroscopy (XPS). It is believed this robust smart surface can find wide applications in surface immobilization of bioactive moieties.

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“…Molecules capable to form SAMs generally consist of three essential parts: the headgroup that binds the ligand to the substrate, the tail group that constitutes the outermost surface of the monolayer film, and the spacer unit that separates the head and tail building blocks and drive the spontaneous molecular assembly, due to intermolecular interactions. Within this general concept, one can combine different moieties and terminal functionalities into simple rigid-rod-like molecules, complex architectures, or even molecular ''devices'', carrying active units which serve as, e.g., electrodes [7], biosensors [8], molecular machines [9,10], or molecular electronics components and devices [11,12].…”

Section: Introductionmentioning

confidence: 99%