Synthesis of a molecular tripod to anchor molecular coordination compounds to semiconductor nanoparticles

Guo, Wenzhuo; Galoppini, Elena; Rydja, Gunilla; Pardi, Gianluca

doi:10.1016/s0040-4039(00)01187-4

Cited by 39 publications

(16 citation statements)

References 14 publications

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“…Here, we utilize a tripodal structure reminiscent to that employed by Tour and co-workers. , This anchoring unit consists of three thiol-substituted diphenyl ethyne units attached to a silicon atom (Scheme ). This design was chosen over other tripodal structures reported previously, − because the silicon atom should reduce potential long distance through-bond interactions with the gold substrate. , In addition, the relatively large structure increases the separation of the switching unit from the surface by an estimated 7 Å (based on density functional theory calculations, vide infra ), thus minimizing through-space interactions with the substrate. In contrast to the design by Tour and co-workers, which has methylene spacers connecting the thiol functionalities to the phenyl groups, we have chosen to attach the thiol functionalities directly to the phenyl groups.…”

Section: Introductionmentioning

confidence: 99%

Position and Orientation Control of a Photo- and Electrochromic Dithienylethene Using a Tripodal Anchor on Gold Surfaces

et al. 2015

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A tripodal system for anchoring photochromic dithienylethenes on gold surfaces is reported. The self-assembled monolayers of a tripod-functionalized dithienylethene were characterized by cyclic voltammetry, surface-enhanced Raman spectroscopy (SERS), and X-ray photoelectron spectroscopy (XPS). These data are compared with solution studies, solid state Raman spectroscopy, and density functional theory (DFT) calculations. We show that the tripod-functionalized dithienylethene forms stable monolayers on gold in which all three legs of the tripod are adsorbed via the thiol units, thus providing a fixed position and orientation of the dithienylethene moiety with respect to the surface. Importantly, immobilization in this way allows for retention of both the photochemical and electrochemical functionality of the dithienylethene unit and reduces photochemical fatigue observed in solution.

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Section: Introductionmentioning

confidence: 99%

Position and Orientation Control of a Photo- and Electrochromic Dithienylethene Using a Tripodal Anchor on Gold Surfaces

et al. 2015

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“…In our system (Figure 1), the movement of a molecule is restricted by attaching the molecule to a surface via a tripod. [20][21][22][23] The molecular caltrops are tetrahedral in shape and can assemble upright on a metallic surface (1) Boyer, P. D. Angew. Chem., Int.…”

Section: Introductionmentioning

confidence: 99%

“…In our system (Figure ), the movement of a molecule is restricted by attaching the molecule to a surface via a tripod. − The molecular caltrops are tetrahedral in shape and can assemble upright on a metallic surface (such as Au) in the form of self-assembled monolayers (SAMs). Each of the three legs of the tripodal platform bears a sulfur-tipped adhesion unit, delivered via an acetyl-protected benzylic thiol.…”

Section: Introductionmentioning

confidence: 99%

En Route to Surface-Bound Electric Field-Driven Molecular Motors

2003

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Four caltrop-shaped molecules that might be useful as surface-bound electric field-driven molecular motors have been synthesized. The caltrops are comprised of a pair of electron donor-acceptor arms and a tripod base. The molecular arms are based on a carbazole or oligo(phenylene ethynylene) core with a strong net dipole. The tripod base uses a silicon atom as its core. The legs of the tripod bear sulfur-tipped bonding units, as acetyl-protected benzylic thiols, for bonding to a gold surface. The geometry of the tripod base allows the caltrop to project upward from a metallic surface after self-assembly. Ellipsometric studies show that self-assembled monolayers of the caltrops are formed on Au surfaces with molecular thicknesses consistent with the desired upright-shaft arrangement. As a result, the zwitterionic molecular arms might be controllable when electric fields are applied around the caltrops, thereby constituting field-driven motors.

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“…Keywords: cross-coupling · palladium · photochromism · thiophene · tripodal ligands involve Pd-catalyzed cross-coupling reactions as key steps. [13,17,18] Generally, small linker units derived from 1,3,5,7-tetraphenyladamantane having the three binding groups attached to the para position of the phenyl residues, already contain an alkyne spacer for the attachment of a chromophore. Then, the chromophore-linker-conjugate is prepared by a Sonogashira coupling reaction of the ethynylsubstituted tripodal linker system with an iodo-or bromosubstituted chromophoric unit.…”

Section: Introductionmentioning

confidence: 99%

Efficient Preparation of Photoswitchable Dithienylethene‐Linker‐Conjugates by Palladium‐Catalyzed Coupling Reactions of Terminal Alkynes with Thienyl Chlorides and Other Aryl Halides

Zastrow

Thyagarajan

Ahmed

et al. 2010

Chemistry An Asian Journal

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Three photochromic dithienylethene-linker-conjugates with an adamantane core containing different spacer lengths and footprint areas with carboxylic anchoring groups are synthesized. The synthetic routes start either from the ethynylene-linker 5 or the iodo-substituted linker 8. Reaction conditions for the final Sonogashira coupling step between ethynylene-linker 5 with the chloro-substituted dithienylethene 4 in the presence of [PdCl(2)(CH(3)CN)(2)]/X-Phos and Cs(2)CO(3) or K(3)PO(4) are optimized using 2-chloro-5-methylthiophene (9) and triethylsilylacetylene or triisopropylsilylacetylene (10a,b) as model compounds. Experimental conditions are found to suppress the activation of the C(sp)-Si bond in TIPS-acetylene 10b, a reaction leading to a subsequent cross-coupling reaction to form by-product 12. Furthermore, activation of the C(sp)-Si bond in the presence of the fluorinated backbone of the chloro-substituted dithienylethene 4 can also be prevented. The photochromic properties of the conjugate 3 and its precursor dithienylethene 7b are also investigated.

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Synthesis of a molecular tripod to anchor molecular coordination compounds to semiconductor nanoparticles

Cited by 39 publications

References 14 publications

Position and Orientation Control of a Photo- and Electrochromic Dithienylethene Using a Tripodal Anchor on Gold Surfaces

Position and Orientation Control of a Photo- and Electrochromic Dithienylethene Using a Tripodal Anchor on Gold Surfaces

En Route to Surface-Bound Electric Field-Driven Molecular Motors

Efficient Preparation of Photoswitchable Dithienylethene‐Linker‐Conjugates by Palladium‐Catalyzed Coupling Reactions of Terminal Alkynes with Thienyl Chlorides and Other Aryl Halides

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