A tower-shaped prototypic molecule designed as an atomically sharp tip for AFM applications

doi:10.1016/S0040-4039(99)01207-1

Tetrahedron Letters

Volume 40, Issue 35, 27 August 1999, Pages 6353-6356

https://doi.org/10.1016/S0040-4039(99)01207-1 Get rights and content

Abstract

The synthesis of macrocycle 1 using a series of Sonogashira coupling reactions is described. This tower-shaped prototypic molecule tapers to a single hydrogen atom and is designed to serve as an atomically sharp molecular tip for atomic force microscopy imaging studies.

The synthesis of macrocycle 1 using a series of Sonogashira coupling reactions is described. The tower-shaped molecule 1 tapers to a single hydrogen atom and is designed to serve as an atomically sharp molecular tip for atomic force microscopy imaging studies.

References (20)

D.T. Colbert et al.
Trends Biotechnol.
(1999)
P. Stutte et al.
Tetrahedron
(1987)
G. Binning et al.
Phys. Rev. Lett.
(1986)
J. Frommer
Angew. Chem., Int. Ed. Engl.
(1992)
S.R. Snyder et al.
Anal. Chem.
(1992)
S.S. Wong et al.
Nature
(1998)
R. Lal et al.
Am. Phys. Soc.
(1994)
K.E. Drexler et al.
Nature
(1990)
H. Dai et al.
Nature
(1996)

There are more references available in the full text version of this article.

Cited by (34)

Synthesis of substituted indazoles and their corresponding tris(indazolyl)borate tripodal ligands as key building blocks for molecular motors
2009, Inorganica Chimica Acta
The synthesis of functionalized indazoles at the 6-position of the indazole ring is developed. Such precursors give access to tris(indazolyl)borate ligands derived from the scorpionate ligands of Trofimenko. These tripodal ligands are truly bifunctional since they can coordinate a metal via the nitrogen centers of the indazolyl rings and be anchored on surfaces on the opposite side through their 6-functionalizations. Three pendant ester or thioether groups were selected to anchor metallic complexes onto, respectively, an oxide or a metallic surface in view of near-field microscopy experiments. These building blocks have been subsequently used as stator in a family of single molecular rotary motors. The architecture of such compounds is centered around half-sandwich complexes of the family of pentaphenylcyclopentadienyl hydrotris(indazolyl)borate ruthenium (II).
Synthesis and properties of polyacetylenes containing carbazolylmethyl groups
2004, Polymer
Novel acetylene monomers containing carbazolymethyl groups, 3,5-bis[(3,6-di-t-butyl)carbazolylmethyl]-1-ethynylbenzene (1), 3-(3,6-di-t-butyl)carbazolylmethyl-1-ethynylbenzene (2), and 4-(3,6-di-t-butyl)carbazolylmethyl-1-ethynylbenzene (3) were synthesized, and polymerized with [(nbd)RhCl]₂–Et₃N, Rh⁺(nbd)[η⁶-C₆H₅B⁻(C₆H₅)₃], and WCl₆-n-Bu₄Sn catalysts. The corresponding polyacetylenes with number-average molecular weights ranging from 1600 to 115,000 were obtained in 18%-quantitative yields. The UV–vis absorption band edge wavelengths of the polymers obtained with W catalyst were longer than those of the Rh-based polymers. The photoluminescence quantum yields of the W-based polymers were 1.1–3.1%, while those of the Rh-based ones were 0.18–4.1%.
Synthesis of tripod-shaped oligo(phenylene)s with multiple ethenyl groups at the bases for chemisorption on hydrogen-terminated silicon surfaces
2003, Tetrahedron Letters
This communication describes an efficient and convergent synthesis of monodisperse, nanometer-sized, and tripod-shaped oligo(phenylene)s with a triallylsilyl group at the base of each leg and a chlorophenyl group at the focal point of the tripod. These molecules were designed as model compounds for the study of chemisorption of rigid molecules containing multiple ethenyl groups on hydrogen-terminated silicon surfaces. The compounds were synthesized from p-chlorophenyl-tris(p-bromophenyl)silane via selective Pd-catalyzed Ishiyama–Miyaura reaction with bis(pinacolato)diboron, followed by Suzuki coupling with aryl dihalides to elongate the legs. The legs were then end-capped with triallylsilyl groups through Suzuki coupling with 4-triallyphenylboronic acid.
Synthetic Routes to Thiol-Functionalized Organic Semiconductors for Molecular and Organic Electronics
2017, Asian Journal of Organic Chemistry
Rigid multipodal platforms for metal surfaces
2016, Beilstein Journal of Nanotechnology
Multifunctional adamantane derivatives as new scaffolds for the multipresentation of bioactive peptides
2015, Journal of Peptide Science

View all citing articles on Scopus

View full text

A tower-shaped prototypic molecule designed as an atomically sharp tip for AFM applications

Abstract

Trends Biotechnol.

Tetrahedron

Phys. Rev. Lett.

Angew. Chem., Int. Ed. Engl.

Anal. Chem.

Nature

Am. Phys. Soc.

Nature

Nature