Eur. J. Inorg. Chem. 2008 · © WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2008 · ISSN 1434–1948

SUPPORTING INFORMATION

Title: The Effects of Pendant vs. Fused Thiophene Attachment upon the Luminescence Lifetimes and Electrochemistry of Tris(2,2'-bipyridine)ruthenium(II) Complexes Author(s): Lasse J. Nurkkala, Robert O. Steen, Henrik K. J. Friberg, Johanna A. Häggström, Paul V. Bernhardt, Mark J. Riley, Simon J. Dunne* Ref. No.: I200800456

S

NH2

O

OS

NHO

OO

O

1) LiAlH4, Et2O, 0°C2) MnO2, CHCl3, rt

S

HN

O

O

O

S

HN

O

O

O

N

2-AcetylpyridineNaOHMeOH, rt

Ethyl chloroformateToluene, ref lux

48% HBrref lux

NS

N

65%

94%

69%

75%

L10

Scheme S1. Synthetic route to 5-pyridin-2-yl[3,2-b]pyridine L10.

SBrO

SBrN

SBrN

S NH

Br

O

DMF, POCl31,1,2,2-tetra-chloroethane125°C

NSBr

Cl

i) n-BuLiii) H2OEt2O, -35 °C

NS Cl

2-PyridylzincbromideTHF, reflux

NS

N

OH

HO

1) NaOH2) TsClacetoneref lux

NH2OHEtOH, reflux

88%

86%

31%

85%

79%L11

Scheme S2. Synthetic route to 6-pyridin-2-yl-thieno[2,3-b]pyridine L11.

S

O

S

OO 1) n-BuLi

2) DMFTHF, -5°C

S

OO

NBr

PPh3

N

O

S

OO

N

S

N

O

S

N

N Decalin®ref lux

S

N N

NaOAc, NH2OH·HClEtOH, ref lux

PPh3

OH

ethylene glycolbenzene, reflux

KHSO4acetone-H2O55°C

97% 99%

83% 62%

86%

75%

20%

1) n-BuLiTHF, 0°C

2) H2O

L12

Br

Scheme S3. Synthetic route to 6-pyridin-2-yl-thieno[3,2-c]pyridine L12.

Figure S1. Collected voltammograms of the studied complexes C1 – C13.

E (mV vs Fc+/0)

-3000-2500-2000-1500-1000 -500 0 500 1000 1500 2000

C1C2C3C4C5C6C7C8C9C10C11C12C13