Organometallics
Article
ligand, such that N and C positions were equivalent. This was modeled
with equal occupancies for carbon and nitrogen in the same sites.
All calculations were performed using the CrystalStructure interface.
(18) (a) Adams, C. J.; Fey, N.; Weinstein, J. A. Inorg. Chem. 2006, 45,
6105. (b) Adams, C. J.; Fey, N.; Harrison, Z. A.; Sazanovich, I. V.;
Towrie, M.; Weinstein, J. A. Inorg. Chem. 2008, 47, 8242. (c) Rachford,
A. A.; Hua, F.; Adams, C. J.; Castellano, F. N. Dalton Trans. 2009,
3950.
4
2
ASSOCIATED CONTENT
Supporting Information
■
(
19) Crystallographic data for CCDC files 1007422−1007423 can be
*
S
Figures, tables, and CIF files giving X-ray crystallographic data
for 2 and 3, crystallographic refinement parameters and
(20) (a) Blight, B. A.; Ko, S.-B.; Lu, J.-S.; Smith, L. F.; Wang, S.
1
19
geometric features for 2 and 3, H NMR and F NMR spectra
for 1−5, and individual cyclic voltammetry traces for 1−5.
Dalton Trans. 2013, 42, 10089. (b) Hudson, Z. M.; Sun, C.; Helander,
M. G.; Amarne, H.; Lu, Z.-H.; Wang, S. Adv. Funct. Mater. 2010, 20,
3
426. (c) Rao, Y.-L.; Schoenmakers, D.; Chang, Y.-L.; Lu, J.-S.; Lu, Z.-
H.; Kang, Y.; Wang, S. Chem. Eur. J. 2012, 18, 11306. (d) Hudson, Z.
M.; Sun, C.; Helander, M. G.; Chang, Y.-L.; Lu, Z.-H.; Wang, S. J. Am.
Chem. Soc. 2012, 134, 13930.
AUTHOR INFORMATION
Corresponding Author
■
(
21) Baker, G. A.; Rachford, A. A.; Castellano, F. N.; Baker, S. N.
ChemPhysChem 2013, 14, 1025.
22) (a) Hasan, K.; Zysman-Colman, E. J. Phys. Org. Chem. 2013, 26,
(
Notes
2
74. (b) Gasperini, M.; Ragaini, F.; Cenini, S. Organometallics 2002,
2
1, 2950.
(
23) Li, L.; Brennessel, W. W.; Jones, W. D. Organometallics 2009,
8, 3492.
24) Pavlishchuk, V. V.; Addison, A. W. Inorg. Chim. Acta 2000, 298,
97.
The authors declare no competing financial interest.
2
(
ACKNOWLEDGMENTS
■
(25) (a) Janzen, D. E.; VanDerveer, D. G.; Mehne, L. F.; da Silva
E.Z.-C. acknowledges the University of St Andrews for financial
support. We thank Johnson Matthey for the grant of precious
metal chemicals.
Filho, D. A.; Bredas, J.-L.; Grant, G. J. Dalton Trans. 2008, 1872.
(b) Ghedini, M.; Pugliese, T.; La Deda, M.; Godbert, N.; Aiello, I.;
Amati, M.; Belviso, S.; Lelj, F.; Accorsi, G.; Barigelletti, F. Dalton
Trans. 2008, 4303.
(26) (a) Wong, W.-Y.; Wang, X.-Z.; He, Z.; Chan, K.-K.; Djurisic, A.
̌ ́
REFERENCES
■
(
1) (a) Baggaley, E.; Weinstein, J. A.; Williams, J. A. G. Coord. Chem.
Rev. 2012, 256, 1762. (b) Liu, Z.; He, W.; Guo, Z. Chem. Soc. Rev.
B.; Cheung, K.-Y.; Yip, C.-T.; Ng, A. M.-C.; Xi, Y. Y.; Mak, C. S. K.;
Chan, W.-K. J. Am. Chem. Soc. 2007, 129, 14372. (b) Wu, W.; Zhang,
J.; Yang, H.; Jin, B.; Hu, Y.; Hua, J.; Jing, C.; Long, Y.; Tian, H. J.
Mater. Chem. 2012, 22, 5382. (c) Islam, A.; Sugihara, H.; Hara, K.;
Singh, L. P.; Katoh, R.; Yanagida, M.; Takahashi, Y.; Murata, S.;
Arakawa, H.; Fujihashi, G. Inorg. Chem. 2001, 40, 5371. (d) Geary, E.
A. M.; McCall, K. L.; Turner, A.; Murray, P. R.; McInnes, E. J. L.; Jack,
L. A.; Yellowlees, L. J.; Robertson, N. Dalton Trans. 2008, 3701.
2
(
013, 42, 1568.
2) (a) Costa, R. D.; Ortí, E.; Bolink, H. J.; Monti, F.; Accorsi, G.;
Armaroli, N. Angew. Chem., Int. Ed. 2012, 51, 8178. (b) Ladouceur, S.;
Zysman-Colman, E. Eur. J. Inorg. Chem. 2013, 2013, 2985.
(
3) (a) Richter, M. M. Chem. Rev. 2004, 104, 3003. (b) Hu, L.; Xu,
G. Chem. Soc. Rev. 2010, 39, 3275.
4) Hagfeldt, A.; Boschloo, G.; Sun, L.; Kloo, L.; Pettersson, H.
Chem. Rev. 2010, 110, 6595.
(
(
27) (a) Brooks, J.; Babayan, Y.; Lamansky, S.; Djurovich, P. I.;
Tsyba, I.; Bau, R.; Thompson, M. E. Inorg. Chem. 2002, 41, 3055.
b) Kvam, P.; Puzyk, M. V.; Balashev, K. P.; Songstad, J.; Lundberg,
C.; Arnarp, J.; Bjork, L.; Gawinecki, R. Acta Chem. Scand. 1995, 49,
35.
28) (a) Rosa, V.; Aviles
Inorg. Chem. 2008, 47, 7734. (b) Rosa, V.; Santos, C. I. M.; Welter, R.;
Aullon, G.; Lodeiro, C.; Aviles, T. Inorg. Chem. 2010, 49, 8699.
c) Paulovicova, A.; El-Ayaan, U.; Shibayama, K.; Morita, T.; Fukuda,
Y. Eur. J. Inorg. Chem. 2001, 2001, 2641.
29) Dai, F.-R.; Chen, Y.-C.; Lai, L.-F.; Wu, W.-J.; Cui, C.-H.; Tan,
G.-P.; Wang, X.-Z.; Lin, J.-T. s.; Tian, H.; Wong, W.-Y. Chem. Asian J.
012, 7, 1426.
30) Graham, K. R.; Yang, Y.; Sommer, J. R.; Shelton, A. H.; Schanze,
K. S.; Xue, J.; Reynolds, J. R. Chem. Mater. 2011, 23, 5305.
31) Rausch, A. F.; Murphy, L.; Williams, J. A. G.; Yersin, H. Inorg.
Chem. 2011, 51, 312.
32) Li, W.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Cai, D.;
Larsen, R. D.; Reider, P. J. J. Org. Chem. 2002, 67, 5394.
(
(
5) McDaniel, N. D.; Bernhard, S. Dalton Trans. 2010, 39, 10021.
6) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013,
(
̈
1
(
13, 5322.
7) DePriest, J.; Zheng, G. Y.; Goswami, N.; Eichhorn, D. M.;
Woods, C.; Rillema, D. P. Inorg. Chem. 2000, 39, 1955.
8) Jenkins, D. M.; Senn, J. F., Jr.; Bernhard, S. Dalton Trans 2012,
1, 8077.
9) Krikorian, M.; Liu, S.; Swager, T. M. J. Am. Chem. Soc. 2014, 136,
952.
10) (a) Niedermair, F.; Stubenrauch, K.; Pein, A.; Saf, R.; Ingolic,
3
(
́
, T.; Aullon, G.; Covelo, B.; Lodeiro, C.
(
4
(
2
́
́
(
(
(
́
E.;
Grogger, W.; Fritz-Popovski, G.; Trimmel, G.; Slugovc, C. J. Mater.
Chem. 2011, 21, 15183. (b) Niedermair, F.; Noormofidi, N.; Lexer, C.;
Saf, R.; Slugovc, C. Polymer 2011, 52, 1874.
2
(
(
11) Ma, D.-L.; Che, C.-M.; Yan, S.-C. J. Am. Chem. Soc. 2008, 131,
835.
12) Balashev, K. P.; Ivanov, M. A.; Taraskina, T. V.; Cherezova, E. A.
Russ. J. Gen. Chem. 2006, 76, 781.
13) Kvam, P.-I.; Puzyk, M. V.; Balashev, K. P.; Songstad, J. Acta
Chem. Scand. 1995, 49, 335.
14) (a) Hasan, K.; Zysman-Colman, E. Inorg. Chem. 2012, 51,
(
1
(
(
(
(
(
33) Kuivila, H. G.; Wiles, R. A. J. Am. Chem. Soc. 1955, 77, 4830.
34) Kajimoto, O.; Saeki, T.; Nagaoka, Y.; Fueno, T. J. Phys. Chem.
(
12560. (b) Hasan, K.; Zysman-Colman, E. Eur. J. Inorg. Chem. 2013,
1977, 81, 1712.
2013, 4421.
̈
(35) Vandromme, L.; Reißig, H.-U.; Groper, S.; Rabe, J. P. Eur. J. Org.
Chem. 2008, 2008, 2049.
(36) Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc.
2005, 127, 18020.
(
15) (a) Shiotsuki, M.; White, P. S.; Brookhart, M.; Templeton, J. L.
J. Am. Chem. Soc. 2007, 129, 4058. (b) Liu, B.; Gao, M.; Dang, L.;
Zhao, H.; Marder, T. B.; Lin, Z. Organometallics 2012, 31, 3410.
(
1
(
2
16) Lohr, T. L.; Piers, W. E.; Parvez, M. Dalton Trans. 2013, 42,
4742.
17) Parmene, J.; Krivokapic, A.; Tilset, M. Eur. J. Inorg. Chem. 2010,
010, 1381.
(37) Sprengers, J. W.; de Greef, M.; Duin, M. A.; Elsevier, C. J. Eur. J.
Inorg. Chem. 2003, 2003, 3811.
(38) CrystalClear-SM Expert v. 2.1; Rigaku Corp., The Woodlands,
TX, USA, 2010−2013.
2
1
dx.doi.org/10.1021/om5006512 | Organometallics 2015, 34, 13−22