The Journal of Organic Chemistry
Note
1
28.14, 130.23, 135.24, 149.81, 156.30, 164.87, 169.22. MS (EI): 567
Muddiman, D. C.; Hofstadler, S. A.; Smith, R. D. J. Am. Chem. Soc.
1997, 119, 11611. (c) Gianneschi, N. C.; Masar, M. S.; Mirkin, C. A.
Acc. Chem. Res. 2005, 38, 825. (d) Cotton, F. A.; Lin, C.; Murillo, C. A.
Acc. Chem. Res. 2001, 34, 759. (e) Fiedler, D.; Leung, D. H.; Bergman,
R. G.; Raymond, K. N. Acc. Chem. Res. 2005, 38, 351. (f) Liu, S.; Han,
Y.-F.; Jin, G.-X. Chem. Soc. Rev. 2007, 36, 1543. (g) Han, Y.; Jia, W.;
Yu, W.; Jin, G. Chem. Soc. Rev. 2009, 38, 3419. (h) Chakrabarty, R.;
Mukherjee, P. S.; Stang, P. J. Chem. Rev. 2011, 111, 6810.
+
+
(M , 4), 568 [(M + 1) , 1], 92 (32), 121 (33), 129 (100), 185 (74),
+
2
5
13 (93); HRMS (EI): exact mass calcd for C H FeN O [M]
33 22 2 4
66.0929, found 566.0931.
Self-Assembly of Hexagon 6. The dipyridyl donor ligand 1 (2.89
mg, 5.10 μmol) and the organoplatinum 120° acceptor 4 (6.84 mg,
.10 μmol) were weighed accurately into a glass vial. To the vial was
added 0.7 mL of CD Cl solvent, and the reaction solution was then
5
2
2
stirred at room temperature for 1 h to yield a homogeneous orange
solution. The solution was then transferred into the NMR tube to
collect H and P NMR spectra. Orange-colored solid product was
obtained by removing the solvent under vacuum. Yield: 9.73 mg, >
(3) (a) Wang, P.; Moorefield, C. N.; Newkome, G. R. Angew. Chem.,
Int. Ed. 2005, 44, 1679. (b) Wang, J.; Li, X.; Lu, X.; Chan, Y.;
Moorefield, C. N.; Wesdemiotis, C.; Newkome, G. R. Chem.Eur. J.
1
31
̈
2011, 17, 4830. (c) You, C.; Wurthner, F. J. Am. Chem. Soc. 2003, 125,
9716. (d) Sun, W.-Y.; Kusukawa, T.; Fujita, M. J. A. Chem. Soc. 2002,
124, 11570. (e) Ulmann, P. A.; Braunschweig, A. B.; Lee, O.-S.;
1
9
9%. H NMR (CD Cl , 400 MHz): δ 1.07 (t, 108H, J = 7.4 Hz), 1.28
2
2
(
br, 72H), 3.98 (s, 9H), 4.30 (s, 15H), 4.70 (s, 6H), 5.11 (s, 6H), 7.50
31
(
br, 24H), 7.63 (br, 12H), 8.43 (s, 6H), 8.64 (br, 12H).
P
Wiester, M. J.; Schatz, G. C.; Mirkin, C. A. Chem. Commun. 2009,
5121. (f) Han, Y.-F.; Jia, W.-G.; Lin, Y.-J.; Jin, G.-X. Organometallics
NMR(CD Cl , 161.9 MHz): δ 13.25 (J
Pt−P
= 2651.9 Hz). CSI-TOF-
2
2
4+
5+
MS, [M − 4OTf] , 1281.87; [M −- 5OTf] , 995.65. Anal. Calcd for
C
C, 44.88; H, 4.65; N, 1.35.
Self-Assembly of Hexagon 7. The donor ligand 1 (2.84 mg, 5.01
μmol) and the 180° acceptor 5 (6.18 mg, 5.00 μmol) were added to
separate glass vials. To the vials containing the donor was added 0.2
mL of CH Cl , and the resulting solution was transferred to the
2
008, 27, 5002. (g) Han, Y.-F.; Li, H.; Jin, G.-X. Chem. Commun. 2010,
H
F Fe N O P Pt S ·H O: C, 45.19; H, 4.78; N, 1.46. Found:
2
16 270 18
3
6
33 12
6
6
2
4
6, 6879.
(
4) (a) Yang, H.-B.; Das, N.; Huang, F.; Hawkridge, A. M.;
Muddiman, D. C.; Stang, P. J. J. Am. Chem. Soc. 2006, 128, 10014.
b) Yang, H.-B.; Hawkridge, A. M.; Huang, S. D.; Das, N.; Bunge, S.
D.; Muddiman, D. C.; Stang, P. J. J. Am. Chem. Soc. 2007, 129, 2120.
c) Zhao, G.-Z.; Chen, L.-J.; Wang, C.-H.; Yang, H.-B.; Ghosh, K.;
(
2
2
(
acceptor vial charged with 0.2 mL of CH Cl . This process was
2
2
Zheng, Y.-Y.; Lyndon, M. M.; Muddiman, D. C.; Stang, P. J.
Organometallics 2010, 29, 6137.
repeated three times with acetone (3 × 0.15 mL) to ensure
quantitative transfer of the donor to the acceptor. The reaction
solution was then stirred at ambient temperature for 1 h to yield a
homogeneous orange solution. Orange-colored solid product was
obtained by removing the solvent under vacuum pump. Yield: 9.02
mg, > 99%. H NMR (acetone-d , 400 MHz): δ 0.97 (t, 216H, J = 7.2
(5) (a) Chi, K.-W.; Addicott, C.; Stang, P. J. J. Org. Chem. 2004, 69,
2910. (b) Huang, F.; Yang, H.-B.; Das, N.; Maran, U.; Arif, A. M.;
Gibson, H. W.; Stang, P. J. J. Org. Chem. 2006, 71, 6623. (c) Yang, H.-
B.; Ghosh, K.; Northrop, B. H.; Zheng, Y.-R.; Lyndon, M. M.;
Muddiman, D. C.; Stang, P. J. J. Am. Chem. Soc. 2007, 129, 14187.
(d) Ghosh, K.; Yang, H.-B.; Northrop, B. H.; Lyndon, M. M.; Zheng,
Y.-R.; Muddiman, D. C.; Stang, P. J. J. Am. Chem. Soc. 2008, 130, 5320.
(e) Zhu, K.; He, J.; Li, S.; Liu, M.; Wang, F.; Zhang, M.; Abliz, Z.;
Yang, H.-B.; Li, N.; Huang, F. J. Org. Chem. 2009, 74, 3905. (f) Xu, X.-
D.; Yang, H.-B.; Zheng, Y.-R.; Ghosh, K.; Lyndon, M. M.; Muddiman,
D. C.; Stang, P. J. J. Org. Chem. 2010, 75, 7373.
1
6
Hz), 1.29 (br, 144H), 3.86 (s, 18H), 4.21 (s, 30H), 4.59 (s, 12H), 4.97
(
s, 12H), 6.99 (s, 24H), 7.68 (br, 24H), 8.28 (s, 12H), 8.89 (br, 24H).
3
1
P NMR (acetone-d , 161.9 MHz): δ 14.22 (J
= 2716.7 Hz). CSI-
6
Pt−P
− , 2556.03. Anal. Calcd for
4OTf]4
+
TOF-MS, [M
C390H516F Fe N O P Pt S : C, 43.29; H, 4.81; N, 1.55. Found:
C, 43.51; H, 4.63; N, 1.35.
36
6
12 60 24 12 12
ASSOCIATED CONTENT
(6) (a) Yang, H.-B.; Ghosh, K.; Zhao, Y.; Northrop, B. H.; Lyndon,
M. M.; Muddiman, D. C.; White, H. S.; Stang, P. J. J. Am. Chem. Soc.
■
*
S
Supporting Information
2
008, 130, 839. (b) Ghosh, K.; Zhao, Y.; Yang, H.-B.; Northrop, B. H.;
CIF file, crystal structure, and crystallographic data of
compound 1; CSI-TOF-MS results of 6 and 7; multinuclear
NMR spectra of new compounds; cyclic voltammetry
White, H. S.; Stang, P. J. J. Org. Chem. 2008, 73, 8553. (c) Ghosh, K.;
Hu, J.; Yang, H.-B.; Northrop, B. H.; White, H. S.; Stang, P. J. J. Org.
Chem. 2009, 74, 4828. (d) Zhao, G.-Z.; Li, Q.-J.; Chen, L.-J.; Tan, H.;
Wang, C.-H.; Lehman, D. A.; Muddiman, D. C.; Yang, H.-B.
Organometallics 2011, 30, 3637.
(
7) Northrop, B. H.; Yang, H.-B.; Stang, P. J. Chem. Commun. 2008,
AUTHOR INFORMATION
■
5896.
(8) (a) Stang, P. J.; Cao, D. H.; Chen, K.; Gray, G. M.; Muddiman,
D. C.; Smith, R. D. J. Am. Chem. Soc. 1997, 119, 5163. (b) Addicott,
C.; Oesterling, I.; Yamamoto, T.; Mullen, K.; Stang, P. J. J. Org. Chem.
2005, 70, 797. (c) Das, N.; Stang, P. J.; Arif, A. M.; Campana, C. F. J.
Org. Chem. 2005, 70, 10440. (d) Jude, H.; Sinclair, D. J.; Das, N.;
Sherburn, M. S.; Stang, P. J. J. Org. Chem. 2006, 71, 4155. (e) Deng,
H.; Doonan, C. J.; Furukawa.; Ferreira, H.; R. B.; Towne, J.; Knobler,
C. B.; Wang, B.; Yaghi, O. M. Science 2010, 327, 846.
ACKNOWLEDGMENTS
■
H.-B.Y. thanks the NSFC (Nos. 21132005 and 20902027),
Shanghai Shuguang Program (No. 09SG25), Innovation
Program of SMEC (No. 10ZZ32), RFDP (No.
2
0100076110004) of Higher Education of China, and “the
(9) (a) Tominaga, M.; Suzuki, K.; Murase, T.; Fujita, M. J. Am. Chem.
Fundamental Research Funds for the Central Universities” for
Soc. 2005, 127, 11950. (b) Murase, T.; Sato, S.; Fujita, M. Angew.
Chem., Int. Ed. 2007, 46, 5133. (c) Sato, S.; Iida, J.; Suzuki, K.;
Kawano, M.; Ozeki, T.; Fujita, M. Science 2006, 313, 1273. (d) Murase,
T.; Sato, S.; Fujita, M. Angew. Chem., Int. Ed. 2007, 46, 1083. (e) Sun,
W.; Kusukawa, T.; Fujita, M. J. A. Chem. Soc. 2002, 124, 11570.
(f) Suzuki, K.; Kawano, M.; Sato, S.; Fujita, M. J. Am. Chem. Soc. 2007,
129, 10652.
(10) Zhao, L.; Ghosh, K.; Zheng, Y.-R.; Stang, P. J. J. Org. Chem.
2009, 74, 8516.
(11) (a) Collinson, M. M. Acc. Chem. Res. 2007, 40, 777. (b) van
Staveren, D. R.; Metzler-Nolte, N. Chem. Rev. 2004, 104, 5931.
(c) Astruc, D. Acc. Chem. Res. 2000, 33, 287. (d) Belin, C.; Astruc, D.
Angew. Chem., Int. Ed. 2006, 45, 132. (e) Ornelas, C.; Mery, D.; Blais,
financial support.
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