Abstract
Oligomers of poly(thiophene) and poly(ortho-phenyleneethynylene) having pendant S = 1/2 semiquinone radicals (as complexes of cobalt(III)) have been prepared and characterized by electron paramagnetic resonance (EPR) spectroscopy and magnetic measurements (superconducting quantum interferences device = SQUID magnetometry). Our results show that exchange coupling of semiquinone groups along a polythiophene backbone is greater than the corresponding coupling along a poly(ortho-phenyleneethynylene) backbone.
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References
H. Iwamura, Pure Appl. Chem. 58, 187 (1986)
J.S. Miller, A.J. Epstein, Angew. Chem. Int. Ed. Engl. 33, 385 (1994)
H. Iwamura, N. Koga, Acc. Chem. Res. 26, 346 (1993)
P. Turek, K. Nozawa, D. Shiomi, K. Awaga, T. Inabe, Y. Maruyama, M. Kinoshita, Chem. Phys. Lett. 180, 327 (1991)
D.E. Williams, Mol. Phys. 16, 145 (1968)
T. Kaneko, K. Iwamura, R. Nishikawa, M. Teraguchi, T. Aoki, Polymer (Guildf). 55, 1097 (2014)
A. Calzolari, Y. Chen, G.F. Lewis, D.B. Dougherty, D.A. Shultz, M. Buongiorno-Nardelli, J. Phys. Chem. B 116, 13141 (2012)
C. Boehme, J.M. Lupton, Nat. Nanotechnol. 8, 612 (2013)
K. Tagami, M. Tsukada, J. Phys. Chem. B 108, 6441 (2004)
N.M. Gallagher, A. Olankitwanit, A. Rajca, J. Org. Chem. 80, 1291 (2015)
S. Horiuchi, Y. Tokura, Nat. Mater. 7, 357 (2008)
H.-Y. Ye, Y. Zhang, S. Noro, K. Kubo, M. Yoshitake, Z.-Q. Liu, H.-L. Cai, D.-W. Fu, H. Yoshikawa, K. Awaga, R.-G. Xiong, T. Nakamura, Sci. Rep. 3, 2249 (2013)
J. Ouyang, C.-W. Chu, C.R. Szmanda, L. Ma, Y. Yang, Nat. Mater. 3, 918 (2004)
A. Bandyopadhyay, A.J. Pal, Appl. Phys. Lett. 82, 1215 (2003)
X. Lv, J. Mao, Y. Liu, Y. Huang, Y. Ma, A. Yu, S. Yin, Y. Chen, Macromolecules 41, 501 (2008)
X. Wan, X. Lv, G. He, A. Yu, Y. Chen, Eur. Polym. J. 47, 1018 (2011)
W. Yan, X. Wan, Y. Xu, X. Lv, Y. Chen, Synth. Met. 159, 1772 (2009)
K. Oyaizu, H. Nishide, Adv. Mater. 21, 2339 (2009)
F. Li, Y. Zhang, S.R. Kwon, J.L. Lutkenhaus, ACS Macro Lett. 5, 337 (2016)
K. Nakahara, K. Oyaizu, H. Nishide, Chem. Lett. 40, 222 (2011)
T. Janoschka, M.D. Hager, U.S. Schubert, Adv. Mater. 24, 6397 (2012)
H. Nishide, S. Iwasa, Y.J. Pu, T. Suga, K. Nakahara, M. Satoh, Electrochim. Acta 50, 827 (2004)
K. Nakahara, J. Iriyama, S. Iwasa, M. Suguro, M. Satoh, E.J. Cairns, J. Power Sour. 165, 398 (2007)
K. Nakahara, S. Iwasa, M. Satoh, Y. Morioka, J. Iriyama, M. Suguro, E. Hasegawa, Chem. Phys. Lett. 359, 351 (2002)
Y. Jing, Y. Liang, S. Gheytani, Y. Yao, Nano Energy 37, 46 (2017)
N. Mataga, Theor. Chim. Acta 10, 372 (1968)
K. Zhang, M.J. Monteiro, Z. Jia, Polym. Chem. 7, 5589 (2016)
E.P. Tomlinson, M.E. Hay, B.W. Boudouris, Macromolecules 47, 6145 (2014)
A. Rajca, Chem. Rev. 94, 871 (1994)
T. Itoh, Y. Jinbo, K. Hirai, H. Tomioka, J. Am. Chem. Soc. 127, 1650 (2005)
A. Rajca, S. Utamapanya, J. Am. Chem. Soc. 115, 10688 (1993)
J. Veciana, C. Rovira, M.I. Crespo, O. Armet, V.M. Domingo, F. Palacio, J. Am. Chem. Soc. 113, 2552 (1991)
A. Rajca, Adv. Phys. Org. Chem. 40, 153–199 (2005)
A. Rajca, Chem. A Eur. J. 8, 4834 (2002)
A. Rajca, S. Rajca, J. Wongsriratanakul, J. Am. Chem. Soc. 121, 6308 (1999)
R.J. Bushby, N. Taylor, R.A. Williams, J. Mater. Chem. 17, 955 (2007)
H. Murata, D. Miyajima, H. Nishide, Macromolecules 39, 6331 (2006)
R.J. Bushby, C.A. Kilner, N. Taylor, M.E. Vale, Tetrahedron 63, 11458 (2007)
H. Nishide, Y. Hozumi, T. Nii, E. Tsuchida, Macromolecules 30, 3986 (1997)
T. Kaneko, H. Abe, M. Teraguchi, T. Aoki, Macromolecules 46, 2583 (2013)
Y. Miura, M. Matsumoto, Y. Ushitani, Y. Teki, T. Takui, K. Itoh, Macromolecules 26, 6673 (1993)
T. Kaneko, T. Makino, H. Miyaji, A. Onuma, M. Teraguchi, T. Aoki, Polyhedron 22, 1845 (2003)
H. Nishide, T. Kaneko, E. Tsuchida, N. Yoshioka, P.M. Lahti, J. Macromol. 27, 3082 (1994)
H. Nishide, T. Maeda, K. Oyaizu, E. Tsuchida, J. Org. Chem. 64, 7129 (1999)
H. Nishide, M. Takahashi, J. Takashima, Y.J. Pu, E. Tsuchida, J. Org. Chem. 64, 7375 (1999)
Y. Morisaki, T. Ishida, Y. Chujo, Polym. J. 35, 501 (2003)
J.W. Verhoeven, P. Pasman, Tetrahedron 37, 943 (1981)
A. Rajca, S. Utamapanya, S. Thayumanavan, J. Am. Chem. Soc. 114, 1884 (1992)
A. Rajca, Science 294, 1503 (2001)
S. Rajca, A. Rajca, J. Wongsriratanakul, P. Butler, S. Choi, J. Am. Chem. Soc. 126, 6972 (2004)
H. Murata, M. Takahashi, K. Namba, N. Takahashi, H. Nishide, J. Org. Chem. 69, 631 (2004)
K. Matsuda, M.T. Stone, J.S. Moore, J. Am. Chem. Soc. 124, 11836 (2002)
C.R. Ray, J.S. Moore, Adv. Polym. Sci. 177, 91 (2005)
D.A. Shultz, M.G. Hollomon, Chem. Mater. 12, 580 (2000)
M. Miyasaka, T. Yamazaki, E. Tsuchida, H. Nishide, Macromolecules 33, 8211 (2000)
H. Nishide, Adv. Mater. 7, 937 (1995)
S.R. Boone, G.H. Purser, H. Chang, M.D. Lowery, D.N. Hendrickson, C.G. Pierpont, J. Am. Chem. Soc. 111, 2292 (1989)
D.A. Shultz, R.K. Kumar, S. Bin-Salamon, M.L. Kirk, Polyhedron 24, 2876 (2005)
D.A. Shultz, K.E. Vostrikova, S.H. Bodnar, H.-J.H.-J. Koo, M.-H.M.-H. Whangbo, M.L. Kirk, E.C. Depperman, J.W. Kampf, J. Am. Chem. Soc. 125, 1607 (2003)
A. Chaudhary, R. Patra, S.P. Rath, Eur. J. Inorg. Chem. 2010, 5211 (2010)
D.A. Shultz, K.E. Vostrikova, S.H. Bodnar, H. Koo, M. Whangbo, M.L. Kirk, E.C. Depperman, J.W. Kampf, J. Am. Chem. Soc. 125, 1607 (2007)
D.A. Shultz, in Magnetism: Molecules to Materials II, ed. by J. S. Miller and M. Drillon (Wiley-VCH, Weinheim, 2003), pp. 281–306
D.N. Hendrickson, C.G. Pierpont, Top. Curr. Chem. 234, 63 (2004)
Y. Mulyana, K.G. Alley, K.M. Davies, B.F. Abrahams, B. Moubaraki, K.S. Murray, C. Boskovic, Dalt. Trans. 43, 2499 (2014)
M. Ruf, B.C. Noll, M.D. Groner, G.T. Yee, C.G. Pierpont, Inorg. Chem. 36, 4860 (1997)
C. Benelli, A. Dei, D. Gatteschi, L. Pardi, Inorganica Chim. Acta 163, 99 (1989)
D.G. Brown, W.D. Hemphill, Inorg. Chem. 18, 2039 (1979)
O.O. Kahn, Molecular Magnetism (VCH Publishers Inc., New York, 1993)
J.A. Weil, J.R. Bolton, J.E. Wertz, Electron Paramagnetic Resonance: Elementary Theory and Practical Applications (Wiley, New York, 1994)
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DAS acknowledges financial support from NSF (CHE-1931291 and CHE-1764181).
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PH and DAS wrote the manuscript. PH prepared and characterized all molecules and polymers.
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Hewitt, P., Shultz, D.A. In Search of Stable, High-Spin Polymers. Appl Magn Reson 51, 1331–1341 (2020). https://doi.org/10.1007/s00723-020-01293-z
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DOI: https://doi.org/10.1007/s00723-020-01293-z