Tetrathiafulvalenes as π-electron donors for intramolecular charge-transfer materials

Advanced Materials

Volumn 11, Issue 1, 1999, Pages 11-23

  Bryce, Martin R ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; CHEMICAL BONDS; DERIVATIVES; GROUND STATE; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; SULFUR COMPOUNDS;

ELECTRON DONORS; TETRATHIAFULVALENE;

AROMATIC COMPOUNDS;

EID: 0033531052     PISSN: 09359648     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-4095(199901)11:1<11::AID-ADMA11>3.0.CO;2-3     Document Type: Article

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97. Many "extended-TTF" [bis(1,3-ditbiole)] systems are known, but their ICT properties are essentially unexplored. They afford interesting prospects as π-donor moieties in this area, because, depending on the structure and length of the conjugated group between the two 1,3-dithiole units, the bis(dithiole) can behave like TTF (two. separate, single-electron waves) or, alternatively, a single, two-electron oxidation process occurs, and the radical cation cannot be detected (as is the case with compound 34). For leading references to the structural and redox properties of this family of donors see: a) [53]. b) M. R. Bryce, A. J. Moore, M. Hasan, G. J. Ashwell, A. T. Fraser, W. Clegg, M. B. Hursthouse, A. I. Karaulov, Angew. Chem. Int. Ed. Engl 1990, 29, 1450. c) M. R. Bryce, A. J. Moore, B. K. Tanner, R. Whitehead. W. Clegg. F. Gerson. A. Lamprecht, S. Pfenninger, Chem. Mater. 1996, 8, 1182, d) A. J, Moore, M. R. Bryce. A, S. Batsanov, A, Green, J. A. K. Howard, M. A. McKervey, P. McGuigan, I. Ledoux, E. Ortí, R. Viruela. P. M. Viruela, B. Tarbit, J. Mater. Chem. 1998, 8, 1173,
98. Many "extended-TTF" [bis(1,3-ditbiole)] systems are known, but their ICT properties are essentially unexplored. They afford interesting prospects as π-donor moieties in this area, because, depending on the structure and length of the conjugated group between the two 1,3-dithiole units, the bis(dithiole) can behave like TTF (two. separate, single-electron waves) or, alternatively, a single, two-electron oxidation process occurs, and the radical cation cannot be detected (as is the case with compound 34). For leading references to the structural and redox properties of this family of donors see: a) [53]. b) M. R. Bryce, A. J. Moore, M. Hasan, G. J. Ashwell, A. T. Fraser, W. Clegg, M. B. Hursthouse, A. I. Karaulov, Angew. Chem. Int. Ed. Engl 1990, 29, 1450. c) M. R. Bryce, A. J. Moore, B. K. Tanner, R. Whitehead. W. Clegg. F. Gerson. A. Lamprecht, S. Pfenninger, Chem. Mater. 1996, 8, 1182, d) A. J, Moore, M. R. Bryce. A, S. Batsanov, A, Green, J. A. K. Howard, M. A. McKervey, P. McGuigan, I. Ledoux, E. Ortí, R. Viruela. P. M. Viruela, B. Tarbit, J. Mater. Chem. 1998, 8, 1173,
99. Many "extended-TTF" [bis(1,3-ditbiole)] systems are known, but their ICT properties are essentially unexplored. They afford interesting prospects as π-donor moieties in this area, because, depending on the structure and length of the conjugated group between the two 1,3-dithiole units, the bis(dithiole) can behave like TTF (two. separate, single-electron waves) or, alternatively, a single, two-electron oxidation process occurs, and the radical cation cannot be detected (as is the case with compound 34). For leading references to the structural and redox properties of this family of donors see: a) [53]. b) M. R. Bryce, A. J. Moore, M. Hasan, G. J. Ashwell, A. T. Fraser, W. Clegg, M. B. Hursthouse, A. I. Karaulov, Angew. Chem. Int. Ed. Engl 1990, 29, 1450. c) M. R. Bryce, A. J. Moore, B. K. Tanner, R. Whitehead. W. Clegg. F. Gerson. A. Lamprecht, S. Pfenninger, Chem. Mater. 1996, 8, 1182, d) A. J, Moore, M. R. Bryce. A, S. Batsanov, A, Green, J. A. K. Howard, M. A. McKervey, P. McGuigan, I. Ledoux, E. Ortí, R. Viruela. P. M. Viruela, B. Tarbit, J. Mater. Chem. 1998, 8, 1173,
100. Many "extended-TTF" [bis(1,3-ditbiole)] systems are known, but their ICT properties are essentially unexplored. They afford interesting prospects as π-donor moieties in this area, because, depending on the structure and length of the conjugated group between the two 1,3-dithiole units, the bis(dithiole) can behave like TTF (two. separate, single-electron waves) or, alternatively, a single, two-electron oxidation process occurs, and the radical cation cannot be detected (as is the case with compound 34). For leading references to the structural and redox properties of this family of donors see: a) [53]. b) M. R. Bryce, A. J. Moore, M. Hasan, G. J. Ashwell, A. T. Fraser, W. Clegg, M. B. Hursthouse, A. I. Karaulov, Angew. Chem. Int. Ed. Engl 1990, 29, 1450. c) M. R. Bryce, A. J. Moore, B. K. Tanner, R. Whitehead. W. Clegg. F. Gerson. A. Lamprecht, S. Pfenninger, Chem. Mater. 1996, 8, 1182, d) A. J, Moore, M. R. Bryce. A, S. Batsanov, A, Green, J. A. K. Howard, M. A. McKervey, P. McGuigan, I. Ledoux, E. Ortí, R. Viruela. P. M. Viruela, B. Tarbit, J. Mater. Chem. 1998, 8, 1173,
101. C. Wang, M. R. Bryce, A. S, Batsanov, C. F. Stanley, A. Beeby, J, A. K, Howard, J. Chem. Soc., Perkin Trans. 2 1997, 1671.
102. a) A. S. Dhindsa, J, P. Badyal, M. R. Bryce, M. C. Petty, A. J. Moore, Y, M. Lvov, J. Chem. Soc., Chem. Commun. 1999, 970,
103. b) A, S. Dhindsa, Y. P. Song, J, P. Badyal, M, R. Bryce, Y. M. Lvov, M. C. Petty, J. Yarwood, Chem. Mater. 1992, 4, 724.
104. c) Y. P. Song, A. S. Dhindsa, M. R, Bryce, M, C. Petty, J. Yarwood, Thin Solid Films, 1992, 210/211, 589.
105. a) A. S. Batsanov, M. R. Bryce, G. Cooke. J. N. Heaton, J. A. K. Howard, J. Chem. Soc., Chem. Commun. 1993, 1701.
106. b) A. S. Batsanov, M. R. Bryce, G, Cooke, A. S. Dhindsa, J. N, Heaton, J. A. K, Howard, A. J. Moore, M. C. Petty, Chem. Mater. 1994, 6, 1419.
107. c) J. A. K.Howard, A. S. Batsanov, M, R. Bryce, J. N. Heaton, Acta Ctyslallogr. C 1994, 50, 1956.
108. d) A. J, Moore, M, R, Bryce, A. S. Batsanov, J. N, Heaton, C. W. Lehrnann. J. A. K. Howard, N. Robertson, A. E. Underbill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541.
109. A. S. Batsanov, M. R. Bryce, J. N. Heaton, A. J. Moore, P. J. Skahara, J. A. K. Howard, E. Ortí, P. M. Viruela, R. Virucla, J. Mater. Chem. 1995, 5, 1689.
110. A. J. Moore, M. R. Bryce, A. S. Balsanov, J. C. Cole, J. A. K. Howard, Synthesis 1995, 675
111. A. Dolbecq, M. Fourmigué. P. Balail, Bull. Soc. Chim Fr. 1996, 113, 83.
112. a) C. Katayama, M. Honda, H. Kumagai, J. Tanaka, G. Sailo, H. Inokuchi, Bull. Chem. Soc. Jpn. 1985, 58, 2272.
113. h) D, A. Clemente, A. Marzotto, J. Mater. Chem. 1996, 6, 941.
114. Reviews: a) B. Tieke, Adv. Mater. 1991, 2, 222. b) M. R. Bryce, M. C. Petty, Nature 1995, 374, 771.
115. Reviews: a) B. Tieke, Adv. Mater. 1991, 2, 222. b) M. R. Bryce, M. C. Petty, Nature 1995, 374, 771.
116. a) A. S. Dhindsa, M. R. Bryce, J. P. Lloyd, M. C. Petty, Thin Solid Films 1988, 165, L97.
117. b)A, S. Dhindsa, M. R. Bryce, H, Ancelin.M. C Petty, J. Yarwood, Langmuir 1990, 6, 1680.
118. L. M. Goldenberg, M. R. Bryce, S. Wegener, M. C. Pelly, J. P.Cresswell, I. K. Lednev, R. F., Hester, J. N. Moore, J. Mater. Chem. 1997, 7, 2033.
119. This was a serendipitous discovery. Concurrent with other groups (G. Rindorf, N. Thorup, K. Lerstrup,K. Bechgaard, Synth. Met. 1989, 30, 391: F. Bertho, D. Talham, A. Robert, S. Megtert, P. Robin, Mol. Cryst. Liq. Cryst. 1988, 156, 339) we initially envisaged amphiphilic TIT derivatives in which terminal carboxylic acid groups would act as the hydrophobic moiety, and the TTF ring would be comparatively hydrophobia. However, because of their ease of synthesis, our first experiments addressed long-chain acyl-TTF systems, and it quickly became apparent thai these derivatives, with a hydrophilic TTF-C(O) head-group and a hydrophobic alkyl tail, were better suited to LB film formation ([63a], and A. S. Dhindsa, G. Cooke, K. Lerstrup, K. Bcchgaard, M. R. Bryce, M. C. Petty, Chem. Mater. 1992, 4, 720).
120. This was a serendipitous discovery. Concurrent with other groups (G. Rindorf, N. Thorup, K. Lerstrup,K. Bechgaard, Synth. Met. 1989, 30, 391: F. Bertho, D. Talham, A. Robert, S. Megtert, P. Robin, Mol. Cryst. Liq. Cryst. 1988, 156, 339) we initially envisaged amphiphilic TIT derivatives in which terminal carboxylic acid groups would act as the hydrophobic moiety, and the TTF ring would be comparatively hydrophobia. However, because of their ease of synthesis, our first experiments addressed long-chain acyl-TTF systems, and it quickly became apparent thai these derivatives, with a hydrophilic TTF-C(O) head-group and a hydrophobic alkyl tail, were better suited to LB film formation ([63a], and A. S. Dhindsa, G. Cooke, K. Lerstrup, K. Bcchgaard, M. R. Bryce, M. C. Petty, Chem. Mater. 1992, 4, 720).
121. This was a serendipitous discovery. Concurrent with other groups (G. Rindorf, N. Thorup, K. Lerstrup,K. Bechgaard, Synth. Met. 1989, 30, 391: F. Bertho, D. Talham, A. Robert, S. Megtert, P. Robin, Mol. Cryst. Liq. Cryst. 1988, 156, 339) we initially envisaged amphiphilic TIT derivatives in which terminal carboxylic acid groups would act as the hydrophobic moiety, and the TTF ring would be comparatively hydrophobia. However, because of their ease of synthesis, our first experiments addressed long-chain acyl-TTF systems, and it quickly became apparent thai these derivatives, with a hydrophilic TTF-C(O) head-group and a hydrophobic alkyl tail, were better suited to LB film formation ([63a], and A. S. Dhindsa, G. Cooke, K. Lerstrup, K. Bcchgaard, M. R. Bryce, M. C. Petty, Chem. Mater. 1992, 4, 720).
122. a) R. Andren, A, I. de Lucas, J. Ganín, N. Martín. J. Orduna. L. Sándiez, C. Seoane, Synth. Met. 1997, 86, 1817.
123. b) A. I. de Lucas, N. Martín, L. Sánchez, C. Seoane, R. Andreu, J. Ganín, J. Orduna, R. Alcaká, B. Villacampa, Tetrahedron 1998, 54, 4665.
124. C. R. Moylan, S. Ermer, S. M. Lovejoy, I.-H. McComb, D. S. Leung, R. Wortmann, P. Krdmer, R. J. Twieg, J. Am. Chem. Soc. 1996, 118, 12950.
125. For leading studies on donor-spacer-TCNQ systems see: a) G. L. Gains, M. P. O'Neil, W. A. Svcc, M. P Niemczyk, M. R. Wasielewski, J. Am. Chem. Soc. 1991, 113, 719. b) Review: N. Martin, C. Seoane, in Handbook of Conductive Organic Molecules and Polymers. Vol. 1 (Ed: N. S. Nalwa), Wiley, New York 1997, Ch. 1, p. 1.
126. For leading studies on donor-spacer-TCNQ systems see: a) G. L. Gains, M. P. O'Neil, W. A. Svcc, M. P Niemczyk, M. R. Wasielewski, J. Am. Chem. Soc. 1991, 113, 719. b) Review: N. Martin, C. Seoane, in Handbook of Conductive Organic Molecules and Polymers. Vol. 1 (Ed: N. S. Nalwa), Wiley, New York 1997, Ch. 1, p. 1.
127. Reviews: a) J, Roncali, J. Mater. Chem. 1997, 7, 2307. b) M. R. Bryce, W. Devonport, L. M. Goldenberg, C. Wang, Chem. Commun. 1998, 945.
128. Reviews: a) J, Roncali, J. Mater. Chem. 1997, 7, 2307. b) M. R. Bryce, W. Devonport, L. M. Goldenberg, C. Wang, Chem. Commun. 1998, 945.
129. a)T. Jørgensen. T. K. Hansen, J. Becher, Chem. Soc. Rev. 1994, 23, 41.
130. b) J. Becher, Z.-T. Li. P. Blanchard, N. Svenstrup, J. Lau, M. B. Nielsen, P. Leridre, Pure Appl. Chem. 1997, 69, 465.