2008, 27, 316; (d) F. A. Cotton, C. Lin and C. A. Murillo, Acc. Chem.
Res., 2001, 34, 759; (e) V. Maurizot, M. Yoshizawa, M. Kawano and
M. Fujita, Dalton Trans., 2006, 2750; (f) J. Hu, L. Ronger, J. H. K. Yip,
Y. K. Wong, D. L. Ma and J. J. Vittal, Organometallics, 2007, 26, 6533;
(g) G. F. Swiegers and T. J. Malefetse, Coord. Chem. Rev., 2002, 225,
91; (h) J. D. Badjic, A. Nelson, S. J. Cantrill, W. B. Turnbull and J. F.
Stoddart, Acc. Chem. Res., 2005, 38, 723; (i) S. J. Cantrill, K. S. Chichak,
A. J. Peters and J. F. Stoddart, Acc. Chem. Res., 2005, 38, 1; (j) M. Fujita,
K. Umemoto, M. Yoshizawa, N. Fujita, T. Kusukawa and K. Biradha,
Chem. Commun., 2001, 509; (k) S. Das and P. K. Bharadwaj, Inorg.
Chem., 2006, 45, 5257; (l) S. Das and P. K. Bharadwaj, Org. Lett., 2005,
7, 1573; (m) D. L. Caulder and K. N. Raymond, J. Chem. Soc., Dalton
Trans., 1999, 1185; (n) D. L. Caulder and K. N. Raymond, Acc. Chem.
Res., 1999, 32, 975; (o) P. N. W. Baxter, J. M. Lehn, G. Baum and D.
Fenske, Chem.–Eur. J., 1999, 5, 102; (p) M. Fujita, Chem. Soc. Rev.,
1998, 27, 417.
2 (a) S. Ghosh and P. S. Mukherjee, J. Org. Chem., 2006, 71, 8412;
(b) P. S. Mukherjee, N. Das and P. J. Stang, J. Org. Chem., 2004,
69, 3526; (c) S. Ghosh, S. R. Batten, D. Turner and P. S. Mukherjee,
Organometallics, 2007, 26, 3252; (d) S. Ghosh and P. S. Mukherjee,
Organometallics, 2007, 26, 3362; (e) K. C. Mondal, M. G. B. Drew and
P. S. Mukherjee, Inorg. Chem., 2007, 46, 5625; (f) S. Ghosh and P. S.
Mukherjee, Tetrahedron Lett., 2006, 47, 9297; (g) S. Ghosh, D. Turner,
S. R. Batten and P. S. Mukherjee, Dalton Trans., 2007, 1869; (h) K. C.
Mondal, Y. Song and P. S. Mukherjee, Inorg. Chem., 2007, 46, 9736;
(i) P. S. Mukherjee, K. S. Min, A. M. Arif and P. J. Stang, Inorg. Chem.,
2004, 43, 6345; (j) K. C. Mondal, O. Sengupta, M. Nethaji and P. S.
Mukherjee, Dalton Trans., 2008, 767; (k) O. Sengupta, R. Chakrabarty
and P. S. Mukherjee, Dalton Trans., 2007, 4514; (l) P. S. Mukherjee,
N. Lopez, A. M. Arif, F. Cervantes-Lee and J. C. Noveron, Chem.
Commun., 2007, 1433; (m) S. Shanmugaraju, A. K. Bar, K-W. Chi and
P. S. Mukherjee, Organometallics, 2010, 29, 2971.
3 (a) S. Koner, E. Zangrando, F. Lloret and N. Ray Chaudhuri, Angew.
Chem., Int. Ed., 2002, 42, 1562; (b) A. K. Ghosh, D. Ghoshal, J. Ribas,
G. Mostafa and N. Ray Chaudhuri, Cryst. Growth Des., 2006, 6, 36;
(c) T. K. Maji, S. Sain, G. Mostafa, T. H. Lu, J. Ribas and N. Ray
Chaudhuri, Inorg. Chem., 2003, 42, 709; (d) K. W. Chi, C. Addicott,
A. M. Arif, N. Das and P. J. Stang, J. Org. Chem., 2003, 68, 9798;
(e) F. M. Tabellion, S. R. Seidel, A. M. Arif and P. J. Stang, J. Am.
Chem. Soc., 2001, 123, 7740; (f) F. M. Tabellion, S. R. Seidel, A. M. Arif
and P. J. Stang, J. Am. Chem. Soc., 2001, 123, 11982; (g) S. Hiraoka and
M. Fujita, J. Am. Chem. Soc., 1999, 121, 10239; (h) M.-C. Brandys and
R. J. Puddephatt, J. Am. Chem. Soc., 2001, 123, 4839; (i) Z. Qin, M. C.
Jennings and R. J. Puddephatt, Inorg. Chem., 2001, 40, 6220; (j) J. W.
Steed, D. R. Turner, and K. J. Wallace, Core Concepts in Supramolecular
Chemistry and Nanochemistry, John Wiley & Sons, Ltd., New York,
2007; (k) C. H. M. Amijs, G. P. M. van Klink and G. van Koten, Dalton
Trans., 2006, 308; (l) M. S. Vickers and P. D. Beer, Chem. Soc. Rev., 2007,
2, 211; (m) K. Y. Ng, A. R. Cowley and P. D. Beer, Chem. Commun.,
2006, 3676; (n) D. Curiel and P. D. Beer, Chem. Commun., 2005, 1909;
(o) A. S. R. Chesman, D. R. Turner, D. J. Price, B. Moubaraki, K. S.
Murray, G. B. Deacon and S. R. Batten, Chem. Commun., 2007, 3541;
(p) A. S. R. Chesman, D. R. Turner, E. I. Izgorodina, S. R. Batten and
G. B. Deacon, Dalton Trans., 2007, 1371.
4 (a) Y. K. Kryschenko, S. R. Seidel, A. M. Arif and P. J. Stang,
J. Am. Chem. Soc., 2003, 125, 5193; (b) P. S. Mukherjee, N. Das, Y.
Kryeschenko, A. M. Arif and P. J. Stang, J. Am. Chem. Soc., 2004, 126,
2464; (c) S. J. Lee, A. Hu and W. Lin, J. Am. Chem. Soc., 2002, 124,
12948; (d) N. Das, P. S. Mukherjee, A. M. Arif and P. J. Stang, J. Am.
Chem. Soc., 2003, 125, 13950.
5 A. K. Bar, B. Gole, S. Ghosh and P. S. Mukherjee, Dalton Trans., 2009,
6701.
6 S. Ghosh and P. S. Mukherjee, Dalton Trans., 2007, 2542.
7 N. L. Narvor and C. Lapinte, Organometallics, 1995, 14,
635.
8 M. Pauvert, P. Laine, M. Jonas and O. Weist, J. Org. Chem., 2004, 69,
543.
9 (a) T. S. Gardner, E. Wenis and J. Lee, J. Org. Chem., 1954, 19, 753;
(b) Y. K. Kryschenko, S. R. Seidel, D. C. Muddiman, A. I. Nepomuceno
and P. J. Stang, J. Am. Chem. Soc., 2003, 125, 9647.
Fig. 11 Quenching efficiency of the analytes. Color codes: blue (1),
red (2). Abbreviations: BA = benzoic acid, AQ = anthraquinone, NT =
4-nitrotoluene, TNT = 1,3,5-trinitrotoluene, PA = picric acid.
first example of a neutral rectangle obtained using Pd–C bond
coordination as a driving force. In addition to this neutral Pd2
molecular rectangle, two more cationic rectangles have been
prepared using an organometallic linear donor 1,4-bis[trans-
(ethynyl)Pd(PEt3)2(NO3)]benzene. Furthermore, we have demon-
strated that the self-assembly of building blocks possessing ethynyl
functionalities can endow suitable architectures with interesting
properties, such as increased electron density and fluorescence.
Complexes 1–2 showed fluorescence behavior and the fluorescence
intensity in solution phase was quenched efficiently and selectively
in the presence of electron deficient nitroaromatics, which are the
common chemical constituents of many commercially available
explosives. Because of the neutral nature of the rectangle 1, there
exists anion free open space to accommodate electron deficient
nitroaromatics. Hence complex 1 showed to be a better receptor
for nitroaromatics compared to complex 2. Moreover, due to
the anionic nature of the donor ethynyl clip, rectangle 1 is
neutral and more electron rich compared to the cationic analogue
2, thereby showing better sensitivity towards electron deficient
nitroaromatics.
Acknowledgements
Authors acknowledge the Department of Science and Technology,
New Delhi, India, for financial support. K.-W. C. acknowledges
Pohang Accelerator Laboratory, Pohang 790-784 (Korea) for
the X-ray diffraction data and WCU program (R33-2008-000-
10003). S.S. is grateful to the CSIR for the fellowship and
A.K.B. acknowledges Mr. Yogesh Patil for fruitful discussion
on structure analysis of 1. Authors acknowledge Prof. Mike
Drew for his help on X-ray data collection of 1,4-bis[trans-
(ethynyl)Pd(PEt3)2(Cl)]benzene. Johnson Matthey Pvt. Ltd., UK,
is gratefully acknowledged for the supply of PdCl2 as loan.
10 L. S. Nancy, E. J. Dana, M. C. Jennings and R. J. Puddephatt, Inorg.
Chem., 2004, 43, 7671.
References
11 G. M. Sheldrick, SADABS, Bruker Nonius Area Detector Scaling
and Absorption Correction, version 2.05; University of Go¨ttingen,
Go¨ttingen, Germany, 1999.
1 (a) J.-M. Lehn, Supramolecular Chemistry, Concept and Perspectives,
VCH, New York, 1995; (b) S. R. Seidel and P. J. Stang, Acc. Chem.
Res., 2002, 35, 972; (c) S. Ghosh and P. S. Mukherjee, Organometallics,
2266 | Dalton Trans., 2011, 40, 2257–2267
This journal is
The Royal Society of Chemistry 2011
©