158014-73-4

Basic information

• Product Name: Benzenamine, 3-[2,2':6',2''-terpyridin]-4'-yl-
• CAS NO: 158014-73-4
• Molecular Formula: C21H16N4
• Molecular Weight: 324.385
• Mol File: 158014-73-4.mol

Chemical Properties

• CAS DataBase Reference: Benzenamine, 3-[2,2':6',2''-terpyridin]-4'-yl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 3-[2,2':6',2''-terpyridin]-4'-yl-(158014-73-4)
• EPA Substance Registry System: Benzenamine, 3-[2,2':6',2''-terpyridin]-4'-yl-(158014-73-4)

Safety Data

• Hazardous Substances Data: 158014-73-4(Hazardous Substances Data)

Upstream product

• 134653-69-3 4'-{[(Trifluoromethyl)sulfonyl]oxy}-2,2':6',2''-terpyridine 
• 30418-59-8 3-Aminophenylboronic acid 
• 149817-62-9 4'-bromo-2,2':6',2''-terpyridine 
• 129077-50-5 4′-(3-nitrophenyl)-2,2′:6′,2″-terpyridine 

Downstream Products

• 385817-42-5 1-(3,5-di-tert-butyl-phenyl)-3-(3-[2,2';6',2'']terpyridin-4'-yl-phenyl)-urea 

Relevant articles and documents

Perylene-based, bis(terpyridine)-ru(ii) complexes: synthesis, electrochemical and photovoltaic properties

Perylene-based, terpyridine-Ru(II) complexes are synthesized and their electrochemical and photoelectrochemical properties are studied; their fabrication into dye-sensitized solar cells are described (DSSCs) and their resultant photovoltaic properties are

The synthesis of 4′-aryl substituted terpyridines by Suzuki cross-coupling reactions: Substituent effects on ligand fluorescence

Several 4′-aryl-substituted 2,2′:6′,2″-terpyridines (tpy-C6H4R) have been prepared by palladium-catalysed cross-coupling of 4′-bromoterpyridine or 4′-triflate-terpyridine (triflate = trifluoromethylsulfonyloxy) with aryl boronic acids or esters, RC6H4B(OR′)2 (R = H, m-NH2, p-CHO, -NO2, -CN, -NMe2, -NPh2). The new ligand 4′-mesityl-terpyridine (mesityl = 2,4,6-trimethylphenyl) was prepared in the same way. Similarly, 4′-bromophenylterpyridine (tpy-φ-Br) has been cross-coupled with aryl halides to generate several new biaryl-substituted terpyridines (tpy-φ-C6H4R where R = H, p-CN, NMe2, NPh2), together with two related compounds with pendent 3- or 4-pyridyl groups (tpy-φ-C6H4-py). For selected compounds, the alternative coupling strategy of reaction of a terpyridine-4-boronate or terpyridine-4-phenylboronate with the appropriate aryl halide has also been investigated (e.g. to prepare tpy-φ-C6H4NO2), but was generally found to be less satisfactory. All of the compounds are fluorescent in the UV region of the spectrum, the biaryl-substituted compounds being only slightly red-shifted compared to the monoaryl systems, but with the further red-shift that accompanies protonation being more significant for the former. Fluorescence lifetimes in solution are in the range 1-5 ns. The emission spectra of the aminobiphenyl-substituted compounds (tpy-φ-C6H4NR″2, where R″ = Me or Ph) display a large red-shift with increasing solvent polarity, suggesting the involvement of an intramolecular charge transfer state, as found previously for the two analogues omitting the phenyl ring (tpy-C6H4NR″2). In contrast to the latter, however, protonation or binding of a Lewis acidic metal ion to the aminobiphenyl compounds serves to quench almost completely their emission.

A remarkably stable hydrogen-bonded porphyrin·iron(terpyridine) ion pair

Even in highly competitive solvents such as DMSO, strong bimolecular association and subsequent fluorescence quenching result from the combination of hydrogen bonding and ion pairing between a porphyrinic bis(carboxylate) dianion and an iron(terpyridine)