168003-69-8

Usage

Type of compound

Heterocyclic organic compound

Derivative of

Phenanthroline

Structural feature

Contains two phenylethynyl groups attached at the 3 and 8 positions of the phenanthroline ring

Common use

As a ligand in coordination chemistry for the synthesis of metal complexes

Field of application

Supramolecular chemistry

Potential applications

Development of novel materials such as luminescent materials, organic semiconductors, and molecular electronics

Biological properties

Investigated for potential as an anticancer agent and other medicinal applications

Upstream product

• 100125-12-0 3,8-dibromo-1,10-phenathroline 
• 536-74-3 phenylacetylene 
• 3757-88-8 tributylstannylethynylbenzene 

Relevant academic research and scientific papers

Tuning the Electronic Properties of Phenanthroline Ligands: 3,8-Bis(arylethynyl)-1,10-Phenanthrolines and their Ru(II) Complexes

Palladium-catalyzed cross-coupling reactions between 3,8-dibromo-1,10-phenanthroline and substituted phenylacetylenes provide a novel family of highly conjugated metal chelators.The electronic transitions of the ligands and their Ru(II) complexes are affe

Synthesis and photophysical properties of 3,8-disubstituted 1,10-phenanthrolines and their ruthenium (II) complexes

The palladium-catalysed cross-coupling reaction between 3,8-dibromo-1,10-phenanthroline with phenylacetylene or 3, 5-bis (trifluoromethyl) phenylboronic acid gives good yields of the 3, 8-disubstituted products. These 1,10-phenanthroline derivatives are used for the formation of novel ruthenium complexes of the type [(tbbpy)2Ru(phenR 2)]2+ [where tbbpy = 4, 4′-di-tert-butyl-2,2′- bipyridine, phen = 1, 10-phenanthroline, R represents the substituents at the 3, 8 positions with bromine, phenylacetylene or 3, 5-bis (trifluoromethyl)phenyl]. All compounds are completely characterised by NMR and UV/Vis spectroscopy, MS, electrochemical measurements and Raman and resonance Raman spectroscopy. The photophysical properties indicate a strong influence of the substitution of the phenanthroline ligand on the absorption, emission and Raman properties. With resonance Raman spectroscopy the localisation of the singlet metal-to-ligand charge-transfer (1MLCT) excited state is determined. The solid-state structures of 3, 8-dibromo-1, 10-phenanthroline (phenBr2) and the corresponding ruthenium complex [(tbbpy)2Ru(phenBr2)] 2+ and a structural motif of f(tbbpy)2- Ru[phen-3,8-bis[3, 5-bis (trifluoromethyl)phenyl]}]2+ are also reported.

Use of the Pd-promoted Extended One-Pot (EOP) synthetic protocol for the modular construction of poly-(arylene ethynylene) co-polymers [-Ar-C≡C-Ar′-C≡C-]n, opto- and electro-responsive materials for advanced technology

We report on the use of our novel multistep/ one-pot/Pd-promoted synthetic strategy, named extended one-pot (EOP), for the preparation of polymeric conjugated systems characterized by a backbone composed of regularly alternating alkyne and arylene moieties of type [-C≡C-A-C≡C-B-]n. The "A" unit (or module) is in charge of impressing mechanical strength, chemical stability and processability to the polymer, while different "B" units (or modules) have been selected to obtain polymers with different functional properties. With this "modular approach" concept, a series of co-poly(arylene ethynylene)s, of general formula [-Ar-C≡C-Ar′-C≡C-]n [Ar = 2,5-bis(octyloxy)benzene; Ar′ = 1,10-phenanthroline, hydroquinone, pyridine, tetrafluorobenzene, dithiophene, benzene, and anthracene] potentially useful for the fabrication of sensory, electroactive and light-emitting materials, have been formed. Investigations of the photophysical properties of these materials, both in solution and in the solid state, have demonstrated a large degree of variation of properties depending on the nature of Ar′ and the extension of the conjugation in the polymeric backbone. This EOP synthetic protocol, with its multiple and sequential one-pot Pd-catalyzed processes, is characterized by a very low catalyst charge loading, a consistent cut-down of reaction times, ease of operation and cost with respect to conventional procedures to obtain ethynylated polymers. Moreover, although it is based on the Pd-catalyzed coupling of organostannanes and aromatic halides (Stille reaction), the EOP synthetic route optimizes and reduces the use of tin, because during the multi-step one-pot process, tin intermediates are in situ formed by complete reconversion of tin by-products generated in the course of the transformation. In addition, after formation and isolation of polymeric materials, tin-containing products are recovered and reused to form new reagents for the delivery of the alkyne moiety into the polymer backbone.