-
1
-
-
35148891216
-
-
For recent discussions of this topic, see:
-
For recent discussions of this topic, see:. Kim C., Facchetti A., and Marks T.J. Science 318 (2007) 76
-
(2007)
Science
, vol.318
, pp. 76
-
-
Kim, C.1
Facchetti, A.2
Marks, T.J.3
-
5
-
-
59649111119
-
-
For recent studies, see:
-
For recent studies, see:. Yan H., Chen Z., Zheng Y., Newman C., Quinn J.R., Dotz F., Kastler M., and Facchetti A. Nature 457 (2009) 679
-
(2009)
Nature
, vol.457
, pp. 679
-
-
Yan, H.1
Chen, Z.2
Zheng, Y.3
Newman, C.4
Quinn, J.R.5
Dotz, F.6
Kastler, M.7
Facchetti, A.8
-
6
-
-
67749110114
-
-
Tang M.L., Mannsfeld S.C.B., Sun Y.-S., Becerril H.A., and Bao Z. J. Am. Chem. Soc. 131 (2009) 882
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 882
-
-
Tang, M.L.1
Mannsfeld, S.C.B.2
Sun, Y.-S.3
Becerril, H.A.4
Bao, Z.5
-
8
-
-
67849094349
-
-
Didane Y., Mehl G.H., Kumagai A., Yoshimoto N., Videlot-Ackermann C., and Brisset H. J. Am. Chem. Soc. 130 (2008) 17681
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 17681
-
-
Didane, Y.1
Mehl, G.H.2
Kumagai, A.3
Yoshimoto, N.4
Videlot-Ackermann, C.5
Brisset, H.6
-
9
-
-
40949096935
-
-
Subramanian S., Park S.K., Parkin S.R., Podzorov V., Jackson T.N., and Anthony J.E. J. Am. Chem. Soc. 130 (2008) 2706
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 2706
-
-
Subramanian, S.1
Park, S.K.2
Parkin, S.R.3
Podzorov, V.4
Jackson, T.N.5
Anthony, J.E.6
-
10
-
-
43249119439
-
-
Tang M.L., Reichardt A.D., Miyaki N., Stoltenberg R.M., and Bao Z. J. Am. Chem. Soc. 130 (2008) 6064
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 6064
-
-
Tang, M.L.1
Reichardt, A.D.2
Miyaki, N.3
Stoltenberg, R.M.4
Bao, Z.5
-
11
-
-
34250683550
-
-
Kim D.H., Lee D.Y., Lee H.S., Lee W.H., Kim Y.H., Han J.I., and Cho K. Adv. Mater. 19 (2007) 678
-
(2007)
Adv. Mater.
, vol.19
, pp. 678
-
-
Kim, D.H.1
Lee, D.Y.2
Lee, H.S.3
Lee, W.H.4
Kim, Y.H.5
Han, J.I.6
Cho, K.7
-
12
-
-
33847182809
-
-
Li Y., Wu Y., Liu P., Prostran Z., Gardner S., and Ong B.S. Chem. Mater. 19 (2007) 418
-
(2007)
Chem. Mater.
, vol.19
, pp. 418
-
-
Li, Y.1
Wu, Y.2
Liu, P.3
Prostran, Z.4
Gardner, S.5
Ong, B.S.6
-
13
-
-
8444229713
-
-
Kelly T.W., Baude P.F., Gerlach C., Ender D.E., Muyres D., Hasse M.A., Vogel D.E., and Theiss S.D. Chem. Mater. 16 (2004) 4413
-
(2004)
Chem. Mater.
, vol.16
, pp. 4413
-
-
Kelly, T.W.1
Baude, P.F.2
Gerlach, C.3
Ender, D.E.4
Muyres, D.5
Hasse, M.A.6
Vogel, D.E.7
Theiss, S.D.8
-
14
-
-
33645648893
-
-
Mcculloch I., Heeney M., Bailey C., Genevicius K., Macdonald I., Shkunov M., Sparrowe D., Tierney S., Wagner R., Zhang W., Chabinyc M.L., Kline R.J., Mcgehee M.D., and Toney M.F. Nat. Mater. 5 (2006) 328
-
(2006)
Nat. Mater.
, vol.5
, pp. 328
-
-
Mcculloch, I.1
Heeney, M.2
Bailey, C.3
Genevicius, K.4
Macdonald, I.5
Shkunov, M.6
Sparrowe, D.7
Tierney, S.8
Wagner, R.9
Zhang, W.10
Chabinyc, M.L.11
Kline, R.J.12
Mcgehee, M.D.13
Toney, M.F.14
-
16
-
-
1242269283
-
-
Murphy A.R., Frecht J.M.J., Chang P., Lee J., and Subramanian V. J. Am. Chem. Soc. 126 (2004) 1596
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 1596
-
-
Murphy, A.R.1
Frecht, J.M.J.2
Chang, P.3
Lee, J.4
Subramanian, V.5
-
17
-
-
25444449828
-
-
Xiao K., Liu Y., Qi T., Zhang W., Wang F., Gao J., Qiu W., Ma Y., Cui G., Chen S., Zhan X., Yu G., Qin J., Hu W., and Zhu D. J. Am. Chem. Soc. 127 (2005) 13281
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 13281
-
-
Xiao, K.1
Liu, Y.2
Qi, T.3
Zhang, W.4
Wang, F.5
Gao, J.6
Qiu, W.7
Ma, Y.8
Cui, G.9
Chen, S.10
Zhan, X.11
Yu, G.12
Qin, J.13
Hu, W.14
Zhu, D.15
-
18
-
-
70349797880
-
-
Liu Y., Wang Y., Wu W., Liu Y., Xi H., Wang L., Qui W., Lu K., Du C., and Yu G. Adv. Funct. Mater. 19 (2009) 1
-
(2009)
Adv. Funct. Mater.
, vol.19
, pp. 1
-
-
Liu, Y.1
Wang, Y.2
Wu, W.3
Liu, Y.4
Xi, H.5
Wang, L.6
Qui, W.7
Lu, K.8
Du, C.9
Yu, G.10
-
19
-
-
53549105554
-
-
Fong H.H., Pozdin V.A., Amassian A., Malliaras G.G., Smilgies D.M., He M., Gasper S., Zhang F., and Sorensen M. J. Am. Chem. Soc. 130 (2008) 13202
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 13202
-
-
Fong, H.H.1
Pozdin, V.A.2
Amassian, A.3
Malliaras, G.G.4
Smilgies, D.M.5
He, M.6
Gasper, S.7
Zhang, F.8
Sorensen, M.9
-
20
-
-
77950595889
-
-
see examples in
-
see examples in Ref. [9].
-
, vol.9
-
-
Ref1
-
21
-
-
17144383168
-
-
Payne M.M., Parkin S.R., Anthony J.E., Kuo C.-C., and Jackson T.N. J. Am. Chem. Soc. 127 (2005) 4986
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 4986
-
-
Payne, M.M.1
Parkin, S.R.2
Anthony, J.E.3
Kuo, C.-C.4
Jackson, T.N.5
-
23
-
-
39349115915
-
-
Chen M.-C., Kim C., Chen S.-Y., Chiang Y.-J., Chung M.-C., Facchetti A., and Marks T.J. J. Mater. Chem. 18 (2008) 1029
-
(2008)
J. Mater. Chem.
, vol.18
, pp. 1029
-
-
Chen, M.-C.1
Kim, C.2
Chen, S.-Y.3
Chiang, Y.-J.4
Chung, M.-C.5
Facchetti, A.6
Marks, T.J.7
-
24
-
-
3042811341
-
-
Sakamoto Y., Suzuki T., Kobayashi M., Gao Y., Fukai Y., Inoue Y., Sato F., and Tokito S. J. Am. Chem. Soc. 126 (2004) 8138
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8138
-
-
Sakamoto, Y.1
Suzuki, T.2
Kobayashi, M.3
Gao, Y.4
Fukai, Y.5
Inoue, Y.6
Sato, F.7
Tokito, S.8
-
25
-
-
6444242950
-
-
Facchetti A., Mushrush M., Yoon M.-H., Hutchison G.R., Ratner M.A., and Marks T.J. J. Am. Chem. Soc. 126 (2004) 13859
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 13859
-
-
Facchetti, A.1
Mushrush, M.2
Yoon, M.-H.3
Hutchison, G.R.4
Ratner, M.A.5
Marks, T.J.6
-
29
-
-
61849156745
-
-
Shukla D., Nelson S.F., Freeman D.C., Rajeswaran M., Ahearn W.G., Meyer D.M., and Carey J.T. Chem. Mater. 20 (2008) 7486
-
(2008)
Chem. Mater.
, vol.20
, pp. 7486
-
-
Shukla, D.1
Nelson, S.F.2
Freeman, D.C.3
Rajeswaran, M.4
Ahearn, W.G.5
Meyer, D.M.6
Carey, J.T.7
-
30
-
-
0042709503
-
-
Mushrush M., Facchetti A., Lefenfeld M., Katz H.E., and Marks T.J. J. Am. Chem. Soc. 125 (2003) 9414
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 9414
-
-
Mushrush, M.1
Facchetti, A.2
Lefenfeld, M.3
Katz, H.E.4
Marks, T.J.5
-
36
-
-
33846205263
-
-
For 7 fused ring example see:
-
For 7 fused ring example see:. He M., and Zhang F. J. Org. Chem. 72 (2007) 442
-
(2007)
J. Org. Chem.
, vol.72
, pp. 442
-
-
He, M.1
Zhang, F.2
-
37
-
-
32244438504
-
-
Sun Y., Ma Y., Liu Y., Lin Y., Wang Z., Wang Y., Di C., Xiao K., Chen X., Qiu W., Zhang B., Yu G., Hu W., and Zhu D. Adv. Funct. Mater. 16 (2006) 426
-
(2006)
Adv. Funct. Mater.
, vol.16
, pp. 426
-
-
Sun, Y.1
Ma, Y.2
Liu, Y.3
Lin, Y.4
Wang, Z.5
Wang, Y.6
Di, C.7
Xiao, K.8
Chen, X.9
Qiu, W.10
Zhang, B.11
Yu, G.12
Hu, W.13
Zhu, D.14
-
38
-
-
33745207784
-
-
Sun Y., Liu Y., Ma Y., Di C., Wang Y., Wu W., Yu G., Hu W., and Zhu D. Appl. Phys. Lett. 88 (2006) 242113
-
(2006)
Appl. Phys. Lett.
, vol.88
, pp. 242113
-
-
Sun, Y.1
Liu, Y.2
Ma, Y.3
Di, C.4
Wang, Y.5
Wu, W.6
Yu, G.7
Hu, W.8
Zhu, D.9
-
39
-
-
36448975283
-
-
Hunziker C., Zhan X., Losio P.A., Figi H., Kwon O., Barlow S., Gunter P., and Marder S.R. J. Mater. Chem. 17 (2007) 4972
-
(2007)
J. Mater. Chem.
, vol.17
, pp. 4972
-
-
Hunziker, C.1
Zhan, X.2
Losio, P.A.3
Figi, H.4
Kwon, O.5
Barlow, S.6
Gunter, P.7
Marder, S.R.8
-
41
-
-
0032507252
-
-
Li X.-C., Sirringhaus H., Garnier F., Holmes A.B., Moratti S.C., Feeder N., Clegg W., Teat S.J., and Friend R.H. J. Am. Chem. Soc. 120 (1998) 2206
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 2206
-
-
Li, X.-C.1
Sirringhaus, H.2
Garnier, F.3
Holmes, A.B.4
Moratti, S.C.5
Feeder, N.6
Clegg, W.7
Teat, S.J.8
Friend, R.H.9
-
42
-
-
41749102174
-
-
Li J., Qin F., Li C.M., Bao Q., Chan-Park M.B., Zhang W., Qin J., and Ong B.S. Chem. Mater. 20 (2008) 2057
-
(2008)
Chem. Mater.
, vol.20
, pp. 2057
-
-
Li, J.1
Qin, F.2
Li, C.M.3
Bao, Q.4
Chan-Park, M.B.5
Zhang, W.6
Qin, J.7
Ong, B.S.8
-
43
-
-
67549088153
-
-
Chen M.-C., Chiang Y.-J., Kim C., Guo Y.-J., Chen S.-Y., Liang Y.-J., Huang Y.-W., Hu T.-S., Lee G.-H., Facchetti A., and Marks T.J. Chem. Commun. (2009) 1846
-
(2009)
Chem. Commun.
, pp. 1846
-
-
Chen, M.-C.1
Chiang, Y.-J.2
Kim, C.3
Guo, Y.-J.4
Chen, S.-Y.5
Liang, Y.-J.6
Huang, Y.-W.7
Hu, T.-S.8
Lee, G.-H.9
Facchetti, A.10
Marks, T.J.11
-
45
-
-
6044272954
-
-
Facchetti A., Yoon M.-H., Stern C.L., Hutchison G.R., Ratner M.A., and Marks T.J. J. Am. Chem. Soc. 126 (2004) 13480
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 13480
-
-
Facchetti, A.1
Yoon, M.-H.2
Stern, C.L.3
Hutchison, G.R.4
Ratner, M.A.5
Marks, T.J.6
-
46
-
-
0034671910
-
-
Facchetti A., Deng Y., Wang A., Koide Y., Sirringhaus H., Marks T.J., and Friend R.H. Angew. Chem. Int. Ed. 39 (2000) 4547
-
(2000)
Angew. Chem. Int. Ed.
, vol.39
, pp. 4547
-
-
Facchetti, A.1
Deng, Y.2
Wang, A.3
Koide, Y.4
Sirringhaus, H.5
Marks, T.J.6
Friend, R.H.7
-
47
-
-
0041914506
-
-
Facchetti A., Yoon M.-H., Stern C.L., Katz H.E., and Marks T.J. Angew. Chem. Int. Ed. 42 (2003) 3900
-
(2003)
Angew. Chem. Int. Ed.
, vol.42
, pp. 3900
-
-
Facchetti, A.1
Yoon, M.-H.2
Stern, C.L.3
Katz, H.E.4
Marks, T.J.5
-
48
-
-
33846063402
-
-
Koh S.E., Delley B., Medvedeva J.E., Facchetti A., Freeman A.J., Marks T.J., and Ratner M.A. J. Phys. Chem. B 110 (2006) 24361
-
(2006)
J. Phys. Chem. B
, vol.110
, pp. 24361
-
-
Koh, S.E.1
Delley, B.2
Medvedeva, J.E.3
Facchetti, A.4
Freeman, A.J.5
Marks, T.J.6
Ratner, M.A.7
-
49
-
-
25844465865
-
-
Letizia J.A., Facchetti A., Stern C.L., Ratner M.A., and Marks T.J. J. Am. Chem. Soc. 127 (2005) 13476
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 13476
-
-
Letizia, J.A.1
Facchetti, A.2
Stern, C.L.3
Ratner, M.A.4
Marks, T.J.5
-
52
-
-
33748297544
-
-
Cai X., Burand M.W., Newman C.R., Da Silva Filho D.A., Pappenfus T.M., Bader M.M., Bredas J.-L., Mann K.R., and Frisbie C.D. J. Phys. Chem. B 110 (2006) 14590
-
(2006)
J. Phys. Chem. B
, vol.110
, pp. 14590
-
-
Cai, X.1
Burand, M.W.2
Newman, C.R.3
Da Silva Filho, D.A.4
Pappenfus, T.M.5
Bader, M.M.6
Bredas, J.-L.7
Mann, K.R.8
Frisbie, C.D.9
-
53
-
-
33646522994
-
-
Jung T., Yoo B., Wang L., Jones B.A., Facchetti A., Wasielewski M.R., Marks T.J., and Dodabalapur A. Appl. Phys. Lett. 88 (2006) 183102
-
(2006)
Appl. Phys. Lett.
, vol.88
, pp. 183102
-
-
Jung, T.1
Yoo, B.2
Wang, L.3
Jones, B.A.4
Facchetti, A.5
Wasielewski, M.R.6
Marks, T.J.7
Dodabalapur, A.8
-
54
-
-
27544476830
-
-
Ando S., Murakami R., Nishida J., Tada H., Inoue Y., Tokito S., and Yamashita Y. J. Am. Chem. Soc. 127 (2005) 14996
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 14996
-
-
Ando, S.1
Murakami, R.2
Nishida, J.3
Tada, H.4
Inoue, Y.5
Tokito, S.6
Yamashita, Y.7
-
55
-
-
17644413162
-
-
Ando S., Nishida J., Tada H., Inoue Y., Tokito S., and Yamashita Y. J. Am. Chem. Soc. 127 (2005) 5336
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 5336
-
-
Ando, S.1
Nishida, J.2
Tada, H.3
Inoue, Y.4
Tokito, S.5
Yamashita, Y.6
-
58
-
-
77950595864
-
-
note
-
DFP-DTT (3) was prepared via Suzuki coupling reaction, see Ref. [17]. Stille coupling route could also provide the title compound in comparison yield.
-
-
-
-
59
-
-
77950594023
-
-
note
-
X-ray crystal structure determinations of compounds 4, 5, and 6 are given in the supporting information of Ref. [11].
-
-
-
-
63
-
-
77950593317
-
-
note
-
2 for 6 h.
-
-
-
-
64
-
-
77950595300
-
-
note
-
See similar examples in Ref. [12].
-
-
-
-
65
-
-
33947177157
-
-
This can be ascribed by the increased molecular polarity of the compounds substituted by these F groups.
-
This can be ascribed by the increased molecular polarity of the compounds substituted by these F groups. Chen H.Z., Ling M.M., Mo X., Shi M.M., Wang M., and Bao Z. Chem. Mater. 19 (2007) 816
-
(2007)
Chem. Mater.
, vol.19
, pp. 816
-
-
Chen, H.Z.1
Ling, M.M.2
Mo, X.3
Shi, M.M.4
Wang, M.5
Bao, Z.6
-
66
-
-
3042811341
-
-
Measured with a Pt working electrode in an o-dichlorobenzene solution using 0.1 mol dm-3 Bu4NPF6 as the supporting electrolyte.
-
Measured with a Pt working electrode in an o-dichlorobenzene solution using 0.1 mol dm-3 Bu4NPF6 as the supporting electrolyte. Sakamoto Y., Suzuki T., Kobayashi M., Gao Y., Fukai Y., Inoue Y., Sato F., and Tokito S. J. Am. Chem. Soc. 126 (2004) 8138
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8138
-
-
Sakamoto, Y.1
Suzuki, T.2
Kobayashi, M.3
Gao, Y.4
Fukai, Y.5
Inoue, Y.6
Sato, F.7
Tokito, S.8
-
68
-
-
45249086150
-
-
Benzothiazolyl (BS) derivatives tend to form coplanar arrangement, for example see In contrast, the carbonyl substituents to the DTT cores are with 30°-55° dihedral angels
-
Benzothiazolyl (BS) derivatives tend to form coplanar arrangement, for example see. Chang Y.-C., Chen Y.-D., Chen C.-H., Wen Y.-S., Lin J.T., Chen H.-Y., Kuo M.-Y., and Chao I. J. Org. Chem. 73 (2008) 4608 In contrast, the carbonyl substituents to the DTT cores are with 30°-55° dihedral angels
-
(2008)
J. Org. Chem.
, vol.73
, pp. 4608
-
-
Chang, Y.-C.1
Chen, Y.-D.2
Chen, C.-H.3
Wen, Y.-S.4
Lin, J.T.5
Chen, H.-Y.6
Kuo, M.-Y.7
Chao, I.8
-
69
-
-
77950596520
-
-
note
-
For crystal structures of compounds 4, 5, and 6, see SI in Ref. [11].
-
-
-
-
70
-
-
16444370557
-
-
The intra- and inter-molecular F-H interactions was also observed in other fluorophenyl thiophenes, for examples, see
-
The intra- and inter-molecular F-H interactions was also observed in other fluorophenyl thiophenes, for examples, see. Crouch D.J., Skabara P.J., Heeney M., McCulloch I., Coles S.J., and Hursthouse M.J. Chem. Commun. (2005) 1465
-
(2005)
Chem. Commun.
, pp. 1465
-
-
Crouch, D.J.1
Skabara, P.J.2
Heeney, M.3
McCulloch, I.4
Coles, S.J.5
Hursthouse, M.J.6
-
71
-
-
77950595405
-
-
note
-
For DFCO-4T in Ref. [14], the twist angles are slightly larger (about 60.3°) than the DTT derivatives. The twisted angles are about ∼52°/53°, 30°/55°, and 45° for 4, 5, and 6, respectively, see Ref. [11].
-
-
-
-
72
-
-
77950594316
-
-
note
-
For compounds 4 and 5, the arrangement of the DTT cores adopt a nearly face-to-face packing motif, see SI in Ref. [11].
-
-
-
-
73
-
-
77950596668
-
-
note
-
For 6, the interplanar angle is 36.5°.
-
-
-
-
75
-
-
77950594956
-
-
note
-
Ambipolar transport in these DTT materials was not observed.
-
-
-
-
76
-
-
77950596649
-
-
note
-
In addition to the larger intermolecular core distance, the less conjugation of DTTs may be responsible for the lower mobilities.
-
-
-
|