N-Heterocyclic Donor- and Acceptor-Type Ligands Based on 2-(1H ...

JOCArticle
7.71-7.53 (m, 9H), 7.29-7.25 (m, 3H), 7.17 (m, 1H), 2.56-2.53
(m, 12H). 13 C NMR (CD 3 CN, 75 MHz) δ 157.1, 156.8, 156.7,
156.5, 153.7, 151.5, 151.4, 151.0, 150.9, 150.5, 150.5, 150.4, 150.4,
150.2, 148.0, 140.4, 136.1, 132.7, 130.3, 130.1, 128.3, 128.2, 128.0,
127.5, 125.0, 124.9, 124.6, 124.2, 123.9, 122.2, 121.4, 120.7,
92.9, 88.2, 20.3, 20.3, 20.2. ESI-TOF MS m/z 982.17 ([M -
PF 6 ] þ ). ESI-HRMS calcd for C 45 H 37 F 6 N 9 O 2 PRu ([M - PF 6 ] þ )
982.1750, found 982.1776.
Bis(4,4 0 -dimethyl-2,2 0 -bipyridine)-{2-(1-(4-((4-nitrophenyl)-
ethynyl)phenyl)-1H-[1,2,3]triazol-4-yl)pyridine}ruthenium(II) Hexafluorophosphate
(18). According to the above st<strong>and</strong>ing general
procedure Ru(dmbpy) 2 Cl 2 (25 mg, 0.046 mmol) <strong>and</strong> 2-(1-(4-((4-
nitrophenyl)ethynyl)phenyl)-1H-[1,2,3]triazol-4-yl)pyridine (15, 17
mg, 0.046 mmol) were reacted 2.5 h to yield the pure complex as red
powder after washing twice with ethanol <strong>and</strong> diethyl ether (40 mg,
77%). 1 H NMR (CD 3 CN, 300 MHz) δ 9.25 (s, 1H), 8.38-8.32 (m,
4H), 8.25-8.21 (m, 2H), 8.17-8.15 (m, 1H), 8.03-8.0 (m, 1H),
7.83-7.73 (m, 7H), 7.71-7.58 (m, 4H), 7.36-7.19 (m, 5H),
2.55-2.51 (m, 12H). 13 C NMR (CD 3 CN, 75 MHz) δ 157.2,
156.8, 156.8, 156.5, 151.7, 151.3, 151.1, 151.1, 150.8, 150.6, 150.4,
Happ et al.
150.3, 150.1, 148.7, 147.6, 138.1, 136.1, 133.4, 132.5, 129.0, 128.3,
128.2, 127.5, 126.2, 124.9, 124.8, 124.6, 124.2, 123.9, 123.8, 123.4,
122.7, 120.8, 92.1, 89.4, 20.3, 20.3. ESI-TOF MS m/z 982.17 ([M -
PF 6 ] þ ). ESI-HRMS calcd for C 45 H 37 F 6 N 9 O 2 PRu ([M - PF 6 ] þ )
982.1750, found 982.1759.
Acknowledgment. Financial support of this work by the
Dutch Polymer Institute (DPI), the Nederl<strong>and</strong>se Organisatie
voor Wetenschappelijk Onderzoek (NWO, VICI award
to U.S.S.), the Fonds der Chemischen Industrie (C.F.), <strong>and</strong>
the Carl-Zeiss Stiftung (D.E.) is kindly acknowledged.
Supporting Information Available: UV-vis absorption <strong>and</strong>
emission spectra for the lig<strong>and</strong>s <strong>and</strong> corresponding ruthenium
complexes, crystallographic data for 17, computational details
of 16a <strong>and</strong> 16b (Cartesian coordinates <strong>and</strong> total energies),
<strong>and</strong> 1 H <strong>and</strong> 13 C NMR spectra of all new compounds. This
material is available free of charge via the Internet at http://
pubs.acs.org.
4038 J. Org. Chem. Vol. 75, No. 12, 2010