640297-84-3

Basic information

• Product Name: 3,8-bis(ethynyl)-1,10-phenanthroline
• Synonyms: 3,8-bis(ethynyl)-1,10-phenanthroline;3,8-Diethynyl-1,10-phenanthroline
• CAS NO: 640297-84-3
• Molecular Formula: C₁₆H₈N₂
• Molecular Weight: 228.24812
• Mol File: 640297-84-3.mol

Chemical Properties

• Melting Point: >250 °C
• Boiling Point: 439.7±40.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• PKA: 4.07±0.10(Predicted)
• CAS DataBase Reference: 3,8-bis(ethynyl)-1,10-phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: 3,8-bis(ethynyl)-1,10-phenanthroline(640297-84-3)
• EPA Substance Registry System: 3,8-bis(ethynyl)-1,10-phenanthroline(640297-84-3)

Safety Data

• Hazardous Substances Data: 640297-84-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics:
3,8-bis(ethynyl)-1,10-phenanthroline is used as a molecular building block for the construction of novel materials in the field of organic electronics. Its fluorescent properties and electronic characteristics contribute to the development of advanced electronic devices and components.
Used in Materials Science:
In the materials science industry, 3,8-bis(ethynyl)-1,10-phenanthroline is utilized as a component in the synthesis of new materials with unique properties. Its structure and electronic nature allow for the creation of materials with potential applications in various areas, such as sensors, energy storage, and optoelectronic devices.
Used as a Potential Ligand for Metal Coordination Complexes:
3,8-bis(ethynyl)-1,10-phenanthroline is employed as a potential ligand for the formation of metal coordination complexes. Its ability to coordinate with metal ions can lead to the development of new complexes with specific properties, useful in areas such as catalysis, molecular recognition, and the construction of supramolecular structures.

Upstream product

• 66-71-7 1,10-Phenanthroline 
• 100125-12-0 3,8-dibromo-1,10-phenathroline 
• 681184-51-0 3,8-bis-(3-hydroxy-3-methylbut-1-yn-1-yl)-1,10-phenanthroline 
• 320573-10-2 3,8-bis(trimethylsilanylethynyl)-[1,10]phenanthroline 

Downstream Products

• 1612886-54-0 3,8-bis((4-((trimethylsilyl)ethynyl)phenyl)ethynyl)-1,10-phenanthroline 
• 1417191-53-7 C₂₄H₁₄N₂OS 
• 686778-01-8 3,8-bis(ethynylgold(I)(triphenylphosphine))-1,10-phenanthroline 
• 850374-68-4 3,8-bis(4-iodo-2,3,5,6-tetramethylphenylethynyl)-[1,10]phenanthroline 

Relevant articles and documents

Photophysical Properties of Oligo(phenylene ethynylene) Iridium(III) Complexes Functionalized with Metal-Anchoring Groups

The electrochemical and photophysical properties of a family of conjugated ligands and their iridium(III) cyclometallated complexes are described. They consist of a series of monocationic IrIII bis-2-phenylpyridine complexes with p-phenylethynyl-1,10-phenanthroline ligands of different length. The structure of these ligands includes terminal acetylthiol or pyridine groups, which can provide good electrical contacts between metal electrodes. Cyclic voltammetry, absorption and emission spectroscopy, laser flash photolysis and density functional theory calculations reveal that the high conjugation of the diimine ligand affords small energy gaps between the frontier orbitals. Nevertheless, the nature of the terminal substituents and the extent of the conjugation in the diimine ligand have little influence on the photophysical features at room temperature. The spectroscopic data and theoretical calculations agree that the charge-transfer nature of the emitting excited state is maintained along the series at room temperature, whereas in rigid matrices ligand-centred states also contribute to the low-temperature emission. The good conducting features of the diimine ligands, the small dependence of the HOMO-LUMO (HOMO = highest occupied molecular orbital, LUMO = lowest unoccupied molecular orbital) gaps of these complexes on the ligands and the charge-transfer nature of the emitting excited state make these complexes promising test beds for the study of photoconducting phenomena in molecular junctions.

Effect of metal complexation on the conductance of single-molecular wires measured at room temperature

The present work aims to give insight into the effect that metal coordination has on the room-temperature conductance of molecular wires. For that purpose, we have designed a family of rigid, highly conductive ligands functionalized with different termina

Synthesis of soluble, linear trisphenanthrolines

The preparation of several soluble, linear trisphenanthrolines is described. The ligands are designed along the HETPHEN concept as precursors for heteroleptic bisphenanthroline metal ion complexes. Hence, they are important building blocks for various sup

Synthesis of ladder polyaromatics as new molecular device candidates

In order to investigate one of the proposed molecular electronics switching mechanisms, we synthesized several molecules whose cores are unable to undergo conformational rotation. Preparation of these molecules, all of which are terminated with the thioac

Segmented multitopic ligands constructed from bipyrimidine, phenanthroline, and terpyridine modules

Starting from bromo-substituted 2,2′-bipyrimidine or 1,10-phenanthroline building blocks, the preparation in a first step of ethynyl grafted molecules allows the production in a second step of multitopic ligands by cross-coupling with difunctionalised chelating molecules. Various combinations allow the interconnection of bipyrimidine to terpyridine, pyrene, or phenanthroline fragments. When two alkyne functions are present, a simple protocol gives a large variety of linear or bent ligands with an increasing number of nitrogen atoms. It was also possible to construct a linear complex capped at the periphery by ruthenium(II) centers and retaining an uncomplexed phenanthroline fragment in its core.

A self-assembled supramolecular optical sensor for Ni(II), Cd(II), and Cr(III)

A new chromogenic supramolecular sensor for transition metals is reported. It is based on a newly designed phenanthroline-containing molecule that self-assembles via an organometallic "clip" into a supramolecular optical sensor for metals.