A purely organic molecular metal based on a hydrogen-bonded charge-transfer complex: Crystal structure and electronic properties of TTF-imidazole-p- chloranil

Angewandte Chemie - International Edition

Volumn 43, Issue 46, 2004, Pages 6343-6346

  Murata, Tsuyoshi ^a   Morita, Yasushi ^a,d   Fukui, Kozo ^d   Sato, Kazunobu ^c   Shiomi, Daisuke ^c   Takui, Takeji ^c   Maesato, Mitsuhiko ^b   Yamochi, Hideki ^b   Saito, Gunzi ^b   Nakasuji, Kazuhiro ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c Osaka Prefecture University   (Japan)

^d JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Conducting materials; Crystal engineering; Hydrogen bonds; Magnetic properties

Indexed keywords

CHARGE TRANSFER; COMPLEXATION; HYDROGEN BONDS; METALS; STACKING FAULTS;

CHLORANIL; COLUMNAR STACKING; ORGANIC MOLECULAR METAL; TETRATHIAFULVALENE;

ORGANIC COMPOUNDS;

CHLORANIL; IMIDAZOLE DERIVATIVE; METAL; ORGANIC COMPOUND;

ARTICLE; CHEMICAL MODIFICATION; CONDUCTANCE; CRYSTAL STRUCTURE; ELECTRON SPIN RESONANCE; ENERGY TRANSFER; HYDROGEN BOND; MOLECULAR INTERACTION; THREE DIMENSIONAL IMAGING;

EID: 19944374438     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460801     Document Type: Article

References (39)

1. a) M. R. Bryce, J. Mater. Chem. 1995, 5, 1481;
2. b) P. Batail, K. Boubekeur, M. Fourmigué, J.-C. P. Gabriel, Chem. Mater. 1998, 10, 3005.
3. For a recent overview of H-bonding, see The Weak Hydrogen Bond (Eds.: G. R. Desiraju, T. Steiner), Oxford University Press, New York, 1999, chap. 1.
4. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
5. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
6. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
7. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
8. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
9. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
10. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
11. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
12. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
13. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
14. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
15. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
16. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
17. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
18. Examples of H-bonded TTF derivatives: Hydroxymethyl: a) P. Blanchard, K. Boubekeur, M. Sallé, G. Duguay, M. Jubault, A. Gorgues, J. D. Martin, E. Canadell, P. Auban-Senzier, D. Jérome, P. Batail, Adv. Mater. 1992, 4, 579. Carboxy: b) A. Dolbecq, M. Fourmigué, P. Batail, Bull. Soc. Chim. Fr. 1996, 133, 83; Amide: c) K. Heuzé, C. Mézière, M. Fourmigué, P. Batail, C. Coulon, E. Canadell, P. Auban-Senzier, D. Jérome, Chem. Mater. 2000, 12, 1898; d) K. Heuzé, M. Fourmigué, P. Batail, E. Canadell, P. Auban-Senzier, Chem. Eur. J. 1999, 5, 2971; e) S. A. Baudron, N. Avarvari, P. Batail, C. Coulon, R. Clérac, E. Canadell, P. Auban-Senzier, J. Am. Chem. Soc. 2003, 125, 11583. Thioamide: f) A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 8, 1541. Nucleic acid: g) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185. Pyrrole-fused: h) K. Zong, W. Chen, M. P. Cava, R. D. Rogers, J. Org. Chem. 1996, 61, 8117; i) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2800, 65, 5794; j) K. A. Nielsen, J. O. Jeppesen, E. Levillain, J. Becher, Angew. Chem. 2003, 115, 197; Angew. Chem. Int. Ed. 2003, 42, 187; for a review, see: k) J. O. Jeppesen, J. Becher, Eur. J. Org. Chem. 2003, 3245. Uracil-fused: l) O. Neilands, S. Belyakov, V. Tilika, A. Edzina, J. Chem. Soc. Chem. Commun. 1995, 325; m) O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065; n) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
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31. -1, which is characteristic of partial CT complexes with segregated stacking columns (see the Supporting Information).
32. [3c]
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35. The ESR spectra observed at all temperatures were reproduced by spectral simulation for a randomly oriented system, which assumes temperature-independent g anisotropy (see text) and temperature-dependent peak-to-peak linewidths (inset of Figure 5).
36. The 2J value was calculated at the UB3LYP/6-31G(d) level according to the procedure developed by Yamaguchi et al.: Y. Takano, T. Taniguchi, H. Isobe, T. Kubo, Y. Morita, K. Yamamoto, K. Nakasuji, T. Takui, K. Yamaguchi, J. Am. Chem. Soc. 2002, 124, 11122, and references therein.
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39. A phase transition in H-bonded CT complex: K. Nakasuji, K. Sugiura, T. Kitagawa, J. Toyoda, H. Okamoto, K. Okaniwa, T. Mitani, H. Yamamoto, I. Murata, A. Kawamoto, J. Tanaka, J. Am. Chem. Soc. 1991, 113, 1862.