Langmuir
ARTICLE
and the Coulombic interactions between TTFꢀTCNQ and ILs.
Both the cation and anion of ILs affect the structure and
properties of the TTFꢀTCNQ/IL gels or mixtures. To the best
of our knowledge, this is the first report on gels made of organic
donor and acceptor without any chemical modification.
Jee, A. Y.; Lee, M.; Lee, S. Chem. Commun. 2009, 5576. (d) Ueno, K.;
Imaizumi, S.; Hata, K.; Watanabe, M. Langmuir 2009, 25, 825.
(e) Nꢀeouze, M. A.; Bideau, J. L.; Gaveau, P.; Bellayer, S.; Vioux, A.
Chem. Mater. 2006, 18, 3931.
(7) (a) Fukushima, T.; Kosaka, A.; Ishimura, Y.; Yamamoto, T.;
Takigawa, T.; Ishii, N.; Aida, T. Science 2003, 300, 2072. (b) Fukushima,
T.; Aida, T. Chem.—Eur. J. 2007, 13, 5048. (c) Wang, J.; Chu, H.; Li, Y.
ACS Nano 2008, 2, 2540.
’ ASSOCIATED CONTENT
(8) (a) Welton, T. Chem. Rev. 1999, 99, 2071. (b) Torimoto, T.;
Tsuda, T.; Okazaki, K.; Kuwabata, S. Adv. Mater. 2010, 22, 1196.
(9) (a) Papagerorgiou, N.; Athanassov, Y.; Armand, M.; Bonho€ute,
P. H.; Pettersson, P.; Azamand, A.; Gr€atzel, M. J. Electrochem. Soc. 1996,
143, 3099. (b) Torimoto, T.; Tsuda, T.; Okazaki, K.; Kuwabata, S. Adv.
Mater. 2010, 22, 1196. (d) Cai, N.; Zhang, J.; Zhou, D.; Yi, Z.; Guo, J.;
Wang, P. J. Phys. Chem. C 2009, 113, 4215. (c) Yamanaka, N.; Kawano,
R.; Kubo, W.; Kitamura, T.; Wada, Y.; Watanabe, M.; Yanagida, S. Chem.
Commun. 2005, 740.
S
Supporting Information. SEM images and UV-Vis-NIR
b
and FTIR absorption spectra of TTFꢀTCNQ/EMSCN, TTFꢀ
TCNQ/EMITf2N, TTFꢀTCNQ/PMII, TTFꢀTCNQ/BMIBF4,
TTFꢀTCNQ/P14,6,6,6Tf2N, and TTFꢀTCNQ/ MOATf2N mix-
tures, as well as XRDs of TTFꢀTCNQ/IL mixtures. This
material is available free of charge via the Internet at http://
pubs.acs.org.
(10) (a) Shin, J. H.; Henderson, W. A.; Passerini, S. Electrochem.
Commun. 2003, 5, 1016. (b) Sirisopanaporn, C.; Fernicola, A.; Scrosati,
B. J. Power Sources 2009, 186, 490. (c) Fernicola, A.; Weise, F. C.;
Greenbaum, S. G.; Kagimoto, J.; Scrosati, B.; Soleto, A. J. Electrochem.
Soc. 2009, 156, A514. (d) Chew, S. Y.; Sun, J.; Wang, J.; Liu, H.; Forsyth,
M.; MacFarlane, D. R. Electrochim. Acta 2008, 53, 6460.
’ AUTHOR INFORMATION
Corresponding Author
*E-mail: mseoj@nus.edu.sg.
(11) (a) Brazier, A.; Appetecchi, G. B.; Passerini, S.; Vuk, A. S.;
Orel, B.; Donsanti, F.; Decker, F. Electrochim. Acta 2007, 52, 4792.
(b) Marcilla, R.; Alcaide, F.; Sardon, H.; Pomposo, J. A.; Pozo-Gonzalo,
C.; Mecerreyes, D. Electrochem. Commun. 2006, 8, 482.
(12) (a) Lauw, Y.; Horne, M. D.; Rodopoulos, T.; Nelson, A.;
Leermakers, F. A. M. J. Phys. Chem. B 2010, 114, 11149. (b) Wei, D.;
Ng, T. W. Electrochem. Commun. 2009, 11, 1996. (c) Simon, P.; Gogotsi,
Y. Nat. Mater. 2008, 7, 845. (d) Balducci, A.; Dugas, R.; Taberna, P. L.;
Simon, P.; Plꢀee, D.; Mastragostino, M.; Passerini, S. J. Power Sources
2007, 165, 922.
’ ACKNOWLEDGMENT
This study was supported by a grant from the Ministry of
Education, Singapore (R-284-000-086-112).
’ REFERENCES
(1) (a) Gansauer, A.; Winkler, I.; Klawonn, T.; Nolte, R. J. M.;
Feiters, M. C.; Borner, H. G.; Hentschel, J.; Dotz, K. H. Organometallics
2009, 28, 1377. (b) Ajayaghosh, A.; Praveen, V. K.; Vijayakumar, C.
Chem. Soc. Rev. 2008, 37, 109.
(13) (a) Ferraris, J.; Cowan, D. O.; Walatka, V.; Porlstein, J. H. J. Am.
Chem. Soc. 1973, 95, 948. (b) Tomkiewicz, Y.; Torrance, J. B.; Scott,
B. A.; Green, D. D. J. Chem. Phys. 1974, 60, 5111.
(2) (a) Kitahara, T.; Shirakawa, M.; Kawano, S.; Beginn, U.; Fujita,
N.; Shinkai, S. J. Am. Chem. Soc. 2005, 127, 14980. (b) Kitamura, T.;
Nakaso, S.; Mizoshita, N.; Tochigi, Y.; Shimomura, T.; Moriyama, M.;
Ito, K.; Kato, T. J. Am. Chem. Soc. 2005, 127, 14769. (c) Wang, C.;
Zhang, D.; Zhu, D. J. Am. Chem. Soc. 2005, 127, 16372. (d) Wang, C.;
Chen, Q.; Sun, F.; Zhang, D.; Zhang, G.; Huang, Y.; Zhao, R.; Zhu, D. J.
Am. Chem. Soc. 2010, 132, 3092. (e) Akutagawa, T.; Kakiuchi, K.;
Hasegawa, T.; Noro, S.; Nakamura, T.; Hasegawa, H.; Mashiko, S.;
Becher, J. Angew. Chem., Int. Ed. 2005, 44, 7283. (f) Akutagawa, T.;
Kakiuchi, K.; Hasegawa, T.; Nakamura, T.; Christensen, C. A.; Becher, J.
Langmuir 2004, 20, 4187. (g) Maitra, U.; Kumar, P. V.; Chandra, N.;
DSouza, L. J.; Prasanna, M. D.; Raju, A. R. Chem. Commun. 1999, 595.
(3) (a) Moniruzzaman, M.; Sahin, A.; Winey, K. I. Carbon 2009,
47, 645. (b) Chen, J.; Xue, C.; Ramasubramaniam, R.; Liu, H. Carbon
2006, 44, 2142. (c) Mei, X.; Ouyang, J. Carbon 2010, 48, 293. (d) Mei,
X.; Cho, S. J.; Fan, B.; Ouyang, J. Nanotechnology 2010, 21, 395202.
(4) (a) Lu, J.; Yan, F.; Texter, J. Prog. Polym. Sci. 2009, 34, 431. (b)
Ste-pniak, I.; Andrzejewska, E. Electrochim. Acta 2009, 54, 5660. (c) Ueki,
T.; Watanabe, M. Macromolecules 2008, 41, 3739. (d) He, Y.; Boswell,
P. G.; B€uhlmann, P.; Lodge, T. P. J. Phys. Chem. B 2007, 111, 4645.
(e) Yeon, S. H.; Kim, K. S.; Choi, S.; Cha, J. H.; Lee, H. J. Phys. Chem. B
2005, 109, 17928.
(5) (a) Jana, S.; Parthiban, A.; Chai, C. L. L. Chem. Commun. 2010,
46, 1488. (b) Mudring, A. V. Aus. J. Chem. 2010, 63, 544. (c) Tu, T.; Bao,
X.; Assenmacher, W.; Peterlik, H.; Daniels, J.; D€otz, K. H. Chem.—Eur. J.
2009, 15, 1853. (d) Sakai, H.; Saitoh, T.; Endo, T.; Tsuchiya, K.; Sakai,
K.; Abe, M. Langmuir 2009, 25, 2601. (e) Puigmartí-Luis, J.; Laukhin, V.;
del Pino, A. P.; Vidal-Gancedo, J.; Rovira, C.; Laukhina, E.; Amabilino,
D. B. Angew. Chem., Int. Ed. 2007, 46, 238. (f) Liu, X. Y. Top. Curr.
Chem. 2005, 256, 1. (g) Ikeda, A.; Sonoda, K.; Ayabe, M.; Tamaru, S.;
Nakashima, T.; Kimizuka, N.; Shinkai, S. Chem. Lett. 2001, 1154.
(6) (a) Ueno, K.; Hata, K.; Katakabe, T.; Kondoh, M.; Watanabe, M.
J. Phys. Chem. B 2008, 112, 9013. (b) Ueno, K.; Inaba, A.; Sano, Y.;
Kondoh, M.; Watanabe, M. Chem. Commun. 2009, 3603. (c) Park, C. L.;
(14) (a) Kistenmacher, T. J.; Phillips, T. E.; Cowan, D. O. Acta
Crystallogr. B 1974, 30, 763. (b) Jerome, D. Chem. Rev. 2004, 104, 5565.
(15) (a) Torrance, J. B.; Scott, B. A.; Welber, B.; Kaufman, F. B.;
Seiden, P. E. Phys. Rev. B 1979, 19, 730. (b) Yakushi, K.; Ugawa, A.;
Ojima, G.; Ida, T.; Tajima, H.; Kuroda, H.; Kato, R.; Kobayashi, H. Mol.
Cryst. Liq. Cryst. 1990, 181, 217. (c) Kim, Y. H.; Jung, S. D.; Chung,
M. A.; Song, K. D.; Cho, D. W. Bull. Korean Chem. Soc. 2008, 29, 948.
(d) Xiao, J. C.; Yin, Z. Y.; Li, H.; Zhang, Q.; Boey, F.; Zhang, H.; Zhang,
Q. C. J. Am. Chem. Soc. 2010, 132, 6926.
(16) (a) Ouyang, J.; Yakushi, K.; Misaki, Y.; Tanaka, K. J. Phys. Soc.
Jpn. 1998, 67, 3191. (b) Ouyang, J.; Dong, J.; Yakushi, K.; Takimiya, K.;
Otsubo, T. J. Phys. Soc. Jpn. 1999, 68, 3708.
(17) (a) Bozio, R.; Girlando, A.; Pecile, D. Chem. Phys. Lett. 1977,
52, 503. (b) Girlando, A.; Marzola, F.; Pecile, C.; Torrance, J. B. J. Chem.
Phys. 1983, 79, 1075.
(18) (a) Bozio, R.; Zanon, I.; Girlando, A.; Pecile, C. J. Chem. Phys.
1979, 71, 2282. (b) Van Duyne, R. P.; Cape, T. W.; Suchanski, M. R.;
Siedle, A. R. J. Phys. Chem. 1986, 90, 739. (c) Ouyang, J.; Yakushi, K.;
Misaki, Y.; Tanaka, K. Phys. Rev. B 2001, 63, 054301. (d) Ouyang, J.;
Yakushi, K.; Kinoshita, T.; Nanbu, N.; Aoyagi, M.; Misaki, Y.; Tanaka, K.
Spectrochim. Acta, Part A 2002, 58, 1643. (e) Yakushi, K.; Yamamoto, K.;
Simonyan, M.; Ouyang, J.; Nakano, C.; Misaki, Y.; Tanaka, K. Phys. Rev.
B 2002, 66, 235102.
(19) Alves, A.; Molinari, A. S.; Xie, H.; Morpurgo, A. F. Nat. Mater.
2008, 7, 574.
(20) Chappell, J. S.; Bloch, A. N.; Bryden, W. A.; Maxfield, M.;
Poehler, T. O.; Cowan, D. O. J. Am. Chem. Soc. 1981, 103, 2442.
(21) (a) Chen, T. H.; Schechtman, B. H. Thin Solid Films 1975,
30, 173. (b) Vollmann, W.; Berger, W.; Hamann, C.; Libera, L. Thin Solid
Films 1984, 111, 7.
(22) Kistenmacher, T. J.; Phillips, T. E.; Cowan, D. O. Acta Crystal-
logr. B 1974, 30, 763.
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dx.doi.org/10.1021/la202465k |Langmuir 2011, 27, 10953–10961