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Novel Semiconducting Biomaterials Derived from a Proline Ester and Tetracyanoquinodimethane Identified by Handpicked Selection of Individual Crystals *
Lisandra L.
Martin
A
D
,
Jinzhen
Lu
A
,
Ayman
Nafady
A
,
Thanh Hai
Le
A
,
Amal I.
Siriwardana
A
B
,
Xiaohu
Qu
A
,
Daouda A. K.
Traore
C
,
Matthew
Wilce
C
and
Alan M.
Bond
A
B
A
School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.
B
ARC Special Research Centre for Green Chemistry, Monash University, Clayton, Vic. 3800, Australia.
C
Department of Biochemistry and Molecular Biology, Monash University, Wellington Road, Clayton, Vic. 3800, Australia.
D
Corresponding author. Email: lisa.martin@monash.edu
Australian Journal of Chemistry
65(7)
935-941 http://dx.doi.org/10.1071/CH12183
Submitted: 5 April 2012 Accepted: 1 May 2012 Published:
2
August
2012
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Abstract
Complex mixtures of cation : anion stoichometries often result from the syntheses of tetracyanoquinodimethane (TCNQ) salts, and often these cannot be easily separated. In this study, the reaction of N,N-dimethyl-d-proline-methylester (Pro(CH3)3+) with LiTCNQ resulted in a mixture of crystals. Hand selection and characterisation of each crystal type by X-ray, infrared, Raman and electrochemistry has provided two stoichometries, 1 : 1 [Pro(CH3)3TCNQ] and 2 : 3 ([(Pro(CH3)3)2(TCNQ)3]). A detailed comparison of these structures is provided. The electrochemical method provides an exceptionally sensitive method of distinguishing differences in stoichiometry. The room temperature conductivity of the mixture is 3.1 × 10–2 S cm–1, which lies in the semiconducting range. 
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References
[1]
M. T. Azcondo, L. Ballester, S. Golhen, A. Gutierrez, L. Ouahab, S. Yartsev, P. Delhaes, J. Mater. Chem. 1999, 9, 1237.
| CrossRef | CAS | 
[2]
X. Qu, A. Nafady, A. Mechler, J. Zhang, A. R. Harris, A. P. O'Mullane, L. L. Martin, A. M. Bond, J. Solid State Electrochem. 2008, 12, 739.
| CrossRef | CAS |
[3]
D. Jerome, Chem. Rev. 2004, 104, 5565.
| CrossRef | CAS |
[4]
P. Cea, S. Martin, A. Villares, D. Mobius, M. C. Lopez, J. Phys. Chem. B 2006, 110, 963.
| CrossRef | CAS |
[5]
Y. Morita, T. Murata, K. Fukui, S. Yamada, K. Sato, D. Shiomi, T. Takui, H. Kitagawa, H. Yamochi, G. Saito, K. Nakasuji, J. Org. Chem. 2005, 70, 2739.
| CrossRef | CAS |
[6]
J. S. Miller, A. J. Epstein, W. M. Reiff, Chem. Rev. 1988, 88, 201.
| CrossRef | CAS |
[7]
D. S. Acker, R. J. Harder, W. R. Hertler, W. Mahler, L. R. Melby, R. E. Benson, W. E. Mochel, J. Am. Chem. Soc. 1960, 82, 6408.
| CrossRef | CAS |
[8]
G. X. Liu, H. Xu, X. M. Ren, W. Y. Sun, CrystEngComm 2008, 10, 1574.
| CrossRef | CAS |
[9]
R. Muller, S. Jonge, K. Myny, D. J. Wouters, J. Genoe, P. Heremans, Solid-State Electron. 2006, 50, 601.
| CrossRef |
[10]
T. Okamoto, M. Kozaki, M. Doe, M. Uchida, G. F. Wang, K. Okada, Chem. Mater. 2005, 17, 5504.
| CrossRef | CAS |
[11]
T. J. Wooster, A. M. Bond, Analyst 2003, 128, 1386.
| CrossRef | CAS |
[12]
T. J. Wooster, A. M. Bond, M. J. Honeychurch, Anal. Chem. 2003, 75, 586.
| CrossRef | CAS |
[13]
G. B. Gardner, D. Venkataraman, J. S. Moore, S. Lee, Nature 1995, 374, 792.
| CrossRef | CAS |
[14]
D. Venkataraman, G. B. Gardner, S. Lee, J. S. Moore, J. Am. Chem. Soc. 1995, 117, 11600.
| CrossRef | CAS |
[15]
O. M. Yaghi, G. M. Li, H. L. Li, Nature 1995, 378, 703.
| CrossRef | CAS |
[16]
A. Padhiyar, A. J. Patel, A. T. Oza, J. Phys. Condens. Matter 2007, 19, 486214.
[17]
X. Qu, J. Lu, C. Zhao, J. F. Boas, B. Moubaraki, K. S. Murray, A. Siriwardana, A. M. Bond, L. L. Martin, Angew. Chem. Int. Ed. 2011, 50, 1589.
| CrossRef | CAS |
[18]
W. Kabsch, J. Appl. Cryst. 1993, 26, 795.
| CrossRef | CAS |
[19]
G. M. Sheldrick, Acta Crystallogr. A 2008, 64, 112.
| CrossRef |
[20]
L. J. Barbour, J. Supramol. Chem. 2001, 1, 189.
| CrossRef | CAS |
[21]
S. Flandrois, D. Chasseau, Acta Crystallogr. B 1977, 33, 2744.
| CrossRef |
[22]
T. J. Kistenmacher, T. J. Emge, A. N. Bloch, D. O. Cowan, Acta Crystallogr. B 1982, 38, 1193.
| CrossRef |
[23]
C. Zhao, A. M. Bond, J. Am. Chem. Soc. 2009, 131, 4279.
| CrossRef | CAS |
[24]
A. Nafady, A. M. Bond, A. P. O'Mullane, Inorg. Chem. 2009, 48, 9258.
| CrossRef | CAS |
[25]
J. Lu, X. Qu, G. Peleckis, J. F. Boas, A. M. Bond, L. L. Martin, J. Org. Chem. 2011, 76, 10078.
| CrossRef | CAS |
|
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