669772-05-8

Upstream product

• 2519-10-0 1,2,3,4,5-pentaphenylcyclopentadiene 
• 56849-84-4 1-bromo-1,2,3,4,5-pentaphenylcyclopenta-2,4-diene 

Downstream Products

• 669772-09-2 bromo [η⁵-1,2,3,4,5-pentakis(p-bromophenyl)cyclopentadienyl dicarbonyl]ruthenium(II) 

Relevant academic research and scientific papers

Preparation of star-shaped pentapyridyl ligands for the formation of giant fullerene-like molecules by coordination chemistry

We present the syntheses of two new star-shaped penta-ligands containing five pyridyls, which may be considered as starting materials for the preparation of fullerene-like molecules by coordination chemistry. One synthetic strategy is similar to that used

Synthesis and reactivity of [penta(4-halogenophenyl)cyclopentadienyl] [hydrotris(indazolyl)borato]ruthenium(II) complexes: Rotation-induced fosbury flop in an organometallic molecular turnstile

The preparation of ruthenium(II) complexes coordinated to a penta(4-halogeno)phenylcyclopentadienyl ligand and to the hydrotris(indazolyl) borate ligand are detailed. Our strategy involves first the coordination of the penta(4-bromo)phenylcyclopentadienyl ligand by reaction with the ruthenium-carbonyl cluster followed by the coordination of the tripodal ligand. The pentabrominated precursor was successfully converted to the pentaiodinated derivative by using the Klapars-Buchwald methodology, applied for the first time on organometallic substrates. Cross-coupling reactions were performed on both pentabromo and pentaiodo complexes to introduce in a single step the five peripheric ferrocenyl fragments required to obtain a potential molecular motor. The two ligands present in the ruthenium complexes undergo a correlated rotation that was established both experimentally by NMR experiments and an Xray diffraction study, and theoretically by DFT calculations. The potentialenergy curve obtained by DFT revealed the energy barrier of the gearing mechanism to be only 4.5 kcal mol-1. These sterically highly constrained complexes can be regarded as organometallic molecular turnstiles.

Technomimetic molecules: Synthesis of ruthenium(II) 1,2,3,4,5-penta(p- bromophenyl)cyclopentadienyl hydrotris(indazolyl)borate, an organometallic molecular turnstile

A short route to prepare a ruthenium complex with a pentaphenyl substituted cyclopentadienyl and a hydrotris(indazolyl)borate ligand is described: this complex can be seen as an organometallic molecular turnstile.

Divergent Synthesis of Molecular Winch Prototypes

We report the synthesis of conceptually new prototypes of molecular winches with the ultimate aim to investigate the work performed by a single ruthenium-based molecular motor anchored on a surface by probing its ability to pull a load upon electrically-driven directional rotation. According to a technomimetic design, the motor was embedded in a winch structure, with a long flexible polyethylene glycol chain terminated by an azide hook to connect a variety of molecular loads. The structure of the motor was first derivatized by means of two sequential cross-coupling reactions involving a penta(4-halogenophenyl)cyclopentadienyl hydrotris(indazolyl)borate ruthenium(II) precursor and the resulting benzylamine derivative was next exploited as key intermediate in the divergent synthesis of a family of nanowinch prototypes. A one-pot method involving sequential peptide coupling and Cu-catalyzed azide-alkyne cycloaddition was developed to yield four loaded nanowinches, with load fragments encompassing triptycene, fullerene and porphyrin moieties.

Expedient Synthesis of Thioether-Functionalized Hydrotris(indazolyl)borate as an Anchoring Platform for Rotary Molecular Machines

Major improvements in the synthesis of surface-mounted rotary molecular machines based on ruthenium(II) complexes are reported. The development of a one-pot indium(III)-mediated “N-deprotection/ester reductive sulfidation” sequence allowed step economy, reproducibility and high efficiency in the synthesis of the thioether-functionalized tripodal ligand. Switching to the thallium salt of hydrotris(indazolyl)borate and to microwave heating further optimized the preparation of the common intermediate in the modular synthesis of symmetric and dissymmetric molecular motors and gears. The penta(4-bromophenyl)cyclopentadienyl ruthenium(II) key precursor is now reproducibly synthesized in 5 steps and 31 % overall yield on the longest linear sequence. Subsequent fivefold Suzuki–Miyaura coupling with ferroceneboronic acid led to a new C5-symmetric pentaferrocenyl molecular motor.