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Sigma-Aldrich

Pyrazino[2,3-f][1,10]phenanthroline

99% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C14H8N4
CAS Number:
217-90-3
Molecular Weight:
232.24
MDL number:
MFCD18447748
UNSPSC Code:
12352103
PubChem Substance ID:
329766739
NACRES:
NA.23

assay

99% (HPLC)

form

solid

mp

310-315 °C

SMILES string

c1cnc2c(c1)c3nccnc3c4cccnc24

InChI

1S/C14H8N4/c1-3-9-11(15-5-1)12-10(4-2-6-16-12)14-13(9)17-7-8-18-14/h1-8H

InChI key

IBOSPAWVGHGUAV-UHFFFAOYSA-N

General description

Pyrazino[2,3-f][1,10]phenanthroline is a ligand which is used in the synthesis of copper(I)- phenanthroline complexes which are used in molecular device technology and in solar-energy conversion. It functions as an electron acceptor and the electron density is delocalized on the quinoxaline ring. The absorption and emission properties and the excited state lifetimes of these phenanthroline based copper complexes can be fine-tuned easily.

Application

  • As an electron accepting ligand in metal complexes which are used in solar cells.
  • Used in the synthesis of ruthenium (II) complexes which are used as DNA probes.

Features and Benefits

Imparts improved directionality of electron transfer in excited copper complexes.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Synthesis, spectroscopic and electrochemical characterization of copper (I) complexes with functionalized pyrazino [2, 3-f]-1, 10-phenanthroline.
Barrientos, L., Araneda, C., Loeb, B., & Crivelli, I. G.
Polyhedron, 27(4), 1287-1295 (2008)
Ge; Hu; Wei;et al.
Journal of Luminescence, 131, 238-243 (2011)
Yujie Sun et al.
Inorganic chemistry, 47(14), 6427-6434 (2008-06-25)
A series of ruthenium(II) complexes possessing ligands with an extended pi system were synthesized and characterized. The complexes are derived from [Ru(bpy)3](2+) (1, bpy = 2,2'-bipyridine) and include [Ru(bpy)2(tpphz)](2+) (2, tpphz = tetrapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]phenazine), [Ru(bpy)2(dppx)](2+) (3, dppx = 7,8-dimethyldipyrido[3,2-a:2',3'-c]phenazine), [Ru(bpy)2(dppm2)](2+) (4

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