S.A. Yao et al. / Polyhedron 58 (2013) 2–6
5
[
m
(C–H)], 1440w, 1345w, 1337mw, 1074m, 1003s [
1203w, 1073w, 1012 m, 994s, 961s, 910br, [ (pyrrole)], 800s,
(phenyl)], 754s, 732m, 704s, 663m.
m(C–N)] 1346w,
Appendix A. Supplementary data
m
[
m
CCDC 875357 contains the supplementary crystallographic data
for Fe(TPP)OAc. These data can be obtained free of charge via
Cambridge Crystallographic Data Centre, 12 Union Road, Cam-
bridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: depos-
it@ccdc.cam.ac.uk. Fig. S1, UV–Vis spectra of Fe(TPP)OAc in
dichloromethane solution upon exposure to air. Supplementary
data associated with this article can be found, in the online version,
4.6. Fe(TPP)OAc
This compound was synthesized as described in the general
procedure with a small modification, using two equivalents of ba-
sic FeIII acetate ([Fe3(
l3-O)(H2O)3(OAc)6]OAc), (0.35 g, 1.5 mmol).
After the solvent was removed, the solid was redissolved in chloro-
form (150 mL) and washed with 20% (v/v) acetic acid (30 mL ꢁ 4)
to ensure that all the
l–O–Fe dimer was converted to monomer,
References
as monitored by TLC; the organic layer was then dried over
Na2SO4; after removal of the solvent, the dark purple solid was col-
lected. Recystallization was performed under nitrogen with dry
CH2Cl2 and hexanes. Yield: (0.53 g, 91%). MS (MALDI-TOF): m/
[1] L. Cheng, G.B. Richter-Addo, in: K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The
Porphyrin Handbook, Academic Press, San Diego, 2000, p. 219.
[2] D. Ostovic´, G.-X. He, T.C. Bruice, in: R.A. Sheldon (Ed.), Metalloporphyrins in
Catalytic Oxidations, Marcel Dekker Inc., New York, 1994, p. 29.
[3] B.R. Cook, T.J. Reinert, K.S. Suslick, J. Am. Chem. Soc. 108 (1986) 7281.
[4] J.P. Collman, Acc. Chem. Res. 10 (1977) 265.
[5] H.B. Dunford, J.S. Stillman, Coord. Chem. Rev. 19 (1976) 187.
[6] G.R. Moore, R.J.P. Williams, Coord. Chem. Rev. 18 (1976) 125.
[7] C. Hu, A. Barabanschikov, M.K. Ellison, J. Zhao, E.E. Alp, W. Sturhahn, M.Z.
Zgierski, J.T. Sage, W.R. Scheidt, Inorg. Chem. 51 (2012) 1359.
[8] N. Lehnert, J.T. Sage, N. Silvernail, W.R. Scheidt, E.E. Alp, W. Sturhahn, J. Zhao,
Inorg. Chem. 49 (2010) 7197.
z = 668.6 [Fe(TPP)]+ꢂ, UV–Vis: k (
e
) = 413 (40000), 504 (2300). Ele-
mental analysis Anal. Calc.: C 75.83%, H 4.43%, N 7.69%. Found: C
75.93%, H 4.23%, N 7.81%. FT-IR (cmꢃ1), [
(C@O)], 1659w, [ (C–
O)], 1276mw, [ (C@C)], 1598w, 1488w [ (C–H)], 1442w, 1367w,
1337mw, 1071m, 1003s [ (C–N)] 1350w, 1200w, 1178w, 1071m,
(pyrrole)], 798s, [ (phenyl)], 755s, 720m,
m
m
m
m
m
994s, 961s, 907br, [
699s, 661m.
m
m
[9] J. Li, Q. Peng, A. Barabanschikov, J.W. Pavlik, E.E. Alp, W. Sturhahn, J. Zhao, C.E.
Schulz, J.T. Sage, W.R. Scheidt, Chem. Eur. J. 17 (2011) 11178.
[10] M. Li, T.J. Neal, G.R.A. Wyllie, A.G. Oliver, C.E. Schulz, W.R. Scheidt, Inorg. Chem.
50 (2011) 9114.
4.7. Co(TPP)
[11] Q. Peng, J.W. Pavlik, W.R. Scheidt, O. Wiest, J. Chem. Theor. Comput. 8 (2012)
214.
[12] I. Turowska-Tyrk, S.-J. Kang, W.R. Scheidt, J. Porphyrins Phthalocyanines 15
(2011) 373.
[13] A.K.S. Tse, K.W. Mak, K.S. Chan, Organometallics 17 (1998) 2651.
[14] J.-H. Chou, M.E. Kosal, H.S. Nalwa, N.A. Rakow, K.S. Suslick, in: K.M. Kadish,
K.M. Smith, R. Guilard (Eds.), The Porphyrin Handbook, Academic Press, San
Diego, 2000, p. 43.
This compound was synthesized as described in the general
procedure, with two equivalents of Co(OAc)2ꢂ4H2O (0.32 g,
1.3 mmol). A pink-purple crystalline solid was collected. Yield:
(0.51 g, 93%). MS (MALDI-TOF): m/z = 671.3 [Co(TPP)]+ꢂ, UV–Vis: k
(e
) = 410 (240000), 528 (32000), Elemental analysis Co(TPP).HOAc,
Anal. Calc.: C 75.61%, H 4.28%, N 7.67%. Found: C 75.67%, H 4.08%, N
7.85%. FT-IR (cmꢃ1), [
(C@C)], 1598w, [ (C–H)], 1442w, 1071m,
1004s [ (C–N)] 1350w, 1071m, 904m [ (pyrrole)], 795s, [ (phe-
[15] A. Rentmeister, T.R. Brown, C.D. Snow, M.N. Carbone, F.H. Arnold,
ChemCatChem 3 (2011).
[16] J.W. Buchler, in: Porphyrins and Metalloporphyrins, Elsevier Scientific Pub. Co.,
Amsterdam, 1975.
[17] J.W. Buchler, in: The Porphyrins, Academic Press, New York, 1978.
[18] J.O. Alben, W.H. Fuchsman, C.A. Beaudreau, W.S. Caughey, Biochemistry 7
(1968) 624.
m
m
m
m
m
nyl)], 749s, 715m, 702s, 671w.
[19] P.J. Crook, A.H. Jackson, G.W. Kenner, Justus Liebigs Ann. Chem. 748 (1971)
142.
4.8. Ni(TPP)
[20] J.W. Buchler, L. Puppe, Justus Liebigs Ann. Chem. 740 (1970) 142.
[21] J.H. Fuhrhop, D. Mauzrall, J. Am. Chem. Soc. 91 (1969) 4174.
[22] J.W. Buchler, M. Folz, H. Habets, J. Van Kaam, K. Rohbock, Chem. Ber. 109
(1976) 1477.
[23] J.W. Buchler, L. Puppe, K. Rohbock, H.H. Schneehage, Ann. NY Acad. Sci. 206
(1973) 116.
[24] A.D. Adler, F.R. Longo, F. Kampas, J. Kim, J. Inorg. Nucl. Chem. 32 (1970)
2443.
[25] H. Oumous, C. Lecomte, J. Portas, P. Cocolios, R. Guilard, Polyhedron 3 (1984)
651.
This compound was synthesized as described in the general
procedure, with two equivalents of Ni(OAc)2ꢂ4H2O (0.40 g,
1.6 mmol). A dark-purple crystalline solid was collected. Yield:
(0.52 g, 98%). MS (MALDI-TOF): m/z = 671.0. [Ni(TPP)]+ꢂ, 1H NMR
(300 MHz, CDCl3) d (ppm): 8.74 (s, 8H, b-pyrrole), 8.13–8.20 (s,
8H, o-phenyl), 7.68 (broad, 12H, m- and p-phenyl) UV–Vis: k
(
e
) = 415 (160000), 524 (30000). FT-IR (cmꢃ1), [
(C–H)], 1440w, 1007s [ (C–N)] 1351w, 1260m, 1077m, [
(phenyl)], 742m, 708m, 696m.
m
(C@C)], 1600w,
(pyr-
[26] V. Pelmenschikov, M.R.A. Blomberg, P.E.M. Siegbahn, R.H. Crabtree, J. Am.
Chem. Soc. 124 (2002) 4039.
[27] C.A. Reed, T. Mashiko, S.P. Bentley, M.E. Kastner, W.R. Scheidt, K. Spartalian, G.
Lang, J. Am. Chem. Soc. 101 (1979) 2948.
[
m
m
m
role)], 793s, [
m
[28] T. Wijesekera, D. Dolphin, in: R.A. Sheldon (Ed.), Metalloporphyrin in Catalytic
Oxidation, Marcel Dekker Inc., New York, 1994, p. 193.
[29] S.E. Creager, R.W. Murray, Inorg. Chem. 24 (1985) 3824.
[30] D.A. Summerville, R.D. Jones, B.M. Hoffman, F. Basolo, J. Am. Chem. Soc. 99
(1977).
[31] E.B. Fleischer, J.M. Palmer, T.S. Srivastava, A. Chatterjee, J. Am. Chem. Soc. 93
(1971) 3162.
[32] W.R. Scheidt, C.A. Reed, Chem. Rev. 81 (1981) 543.
[33] W. Hieringer, K. Flechtner, A. Kretschmann, K. Seufert, W. Auwarter, J.V.
Barth, A. Gorling, H.-P. Steinruck, J.M. Gottfried, J. Am. Chem. Soc. 133 (2011)
6206.
4.9. Cu(TPP)
This compound was synthesized as described in general proce-
dure, with two equivalents of Cu(OAc)2ꢂH2O (0.32 g, 1.6 mmol). A
purple crystalline solid was collected. Yield: (0.51 g, 96%). MS
(MALDI-TOF): m/z = 676.4. [Cu(TPP)]+ꢂ, UV–Vis:
k (e) = 414.0
(637000), 537.9 (18200), Elemental analysis Calc.: C 78.15%, H
4.27%, N 8.28%. Found: C 78.06, H 4.21, N 8.38%. FT-IR (cmꢃ1),
[34] A. Ikezaki, M. Nakamura, Chem. Lett. 34 (2005) 1046.
[35] S.A. Vail, D.I. Schuster, D.M. Guldi, M. Isosomppi, N. Tkachenko, H.
Lemmetyinen, A. Palkar, L. Echegoyen, X. Chen, J.Z.H. Zhang, J. Phys. Chem. B
110 (2006) 14155.
[
m(C@C)], 1597w,
[m
(C–H)], 1443w, 1005s
[m(C–N)] 1346m,
(phenyl)], 740m, 710s, 695s, 657m.
1077m, [ (pyrrole)], 792s, [
m
m
[36] B.F.O. Nascimento, M. Pineiro, A.M.d’A. Rocha Gonsalves, M.R. Silva, A.M. Beja,
J.A. Paixao, J. Porphyrins Phthalocyanines 11 (2007) 77.
[37] A.M.J. Devoille, J.B. Love, Dalton Trans. 41 (2012) 65.
[38] J.W. Leeland, A.M.Z. Slawin, J.B. Love, Organometallics 29 (2010) 714.
[39] J.W. Leeland, F.J. White, J.B. Love, J. Am. Chem. Soc 133 (2011) 7320.
[40] S.D. Reid, C. Wilson, A.J. Blake, J.B. Love, Dalton Trans. 39 (2010) 418.
Acknowledgments
We thank the National Science Foundation for financial support
under CHE-10471748.