n-Channel Polymers by Design: Optimizing the Interplay of Solubilizing Substituents, Crystal Packing, and Field-Effect Transistor Characteristics in Polymeric Bithiophene-Imide Semiconductors

Joseph A. Letizia; Michael R. Salata; Caitlin M. Tribout; Antonio Facchetti; Mark A. Ratner; Tobin J. Marks

doi:10.1021/ja710815a

journal article Jul 01, 2008

n-Channel Polymers by Design: Optimizing the Interplay of Solubilizing Substituents, Crystal Packing, and Field-Effect Transistor Characteristics in Polymeric Bithiophene-Imide Semiconductors

Joseph A. Letizia Michael R. Salata Caitlin M. Tribout Antonio Facchetti

Mark A. Ratner

Tobin J. Marks

Journal of the American Chemical Society Vol. 130 No. 30 pp. 9679-9694 · American Chemical Society (ACS)

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References

91

[1]

Bao Z. R. J. Mater. Chem. (1999) 10.1039/a902652e

[2]

Kampen T. U. (2007)

[3]

bConducting Organic Materials and Devices;Jain, S. C., Willander, M., and Kumar, V., Eds.Elsevier Science:New York,2007; Vol.81, p196.

[4]

Charge transport in polymeric transistors

Alberto Salleo

Materials Today 2007 10.1016/s1369-7021(07)70018-4

[5]

dOrganic Electronics;Klauk, H., Ed.Wiley-VCH:Weinheim,2006; p428.

[6]

De Leeuw D. M. Nat. Mater. (2004) 10.1038/nmat1061

[7]

Kelley T. W. Chem. Mater. (2004) 10.1021/cm049614j

[8]

Dimitrakopoulos C. D. Adv. Mater. (2002) 10.1002/1521-4095(20020116)14:2<99::aid-adma99>3.0.co;2-9

[9]

hPrinted Organic and Molecular Electronics;Gamota, D. R., Brazis, P., and Kalyanasundaram, K.,Zhang, J., Eds.Springer:New York,2004; p720.

[10]

Fix W. Appl. Phys. Lett. (2002) 10.1063/1.1501450

[11]

Gelinck G. H. Appl. Phys. Lett. (2000) 10.1063/1.1290728

[12]

Fichou D. (1999)

[13]

Skotheim T. A. (1998)

[14]

Processible conjugated polymers: from organic semiconductors to organic metals and superconductors

Adam Pron, Patrice Rannou

Progress in Polymer Science 2001 10.1016/s0079-6700(01)00043-0

[15]

Sze S. M. (2002)

[16]

Bao Z. N. Nat. Mater. (2004) 10.1038/nmat1079

[17]

Chabinyc M. L. Chem. Mater. (2004) 10.1021/cm049647z

[18]

Forrest S. R. Nature (2004) 10.1038/nature02498

[19]

Kawase T. Adv. Mater. (2001) 10.1002/1521-4095(200111)13:21<1601::aid-adma1601>3.0.co;2-x

[20]

Knobloch A. J. Appl. Phys. (2004) 10.1063/1.1767291

[21]

Meijer E. J. Nat. Mater. (2003) 10.1038/nmat978

[22]

Sirringhaus H. Science (2000) 10.1126/science.290.5499.2123

[23]

Hadziioannou, G., and Malliaras, G. G.Semiconducting Polymers;Wiley-VCH:New York,2006; p743.

[24]

Bao Z. Adv. Mater. (2000) 10.1002/(sici)1521-4095(200002)12:3<227::aid-adma227>3.0.co;2-u

[25]

Usta H. J. Am. Chem. Soc. (2006) 10.1021/ja062908g

[26]

Sirringhaus H. Science (1998) 10.1126/science.280.5370.1741

[27]

Veres J. Chem. Mater. (2004) 10.1021/cm049598q

[28]

Ong B. S. J. Am. Chem. Soc. (2004) 10.1021/ja039772w

[29]

McCulloch I. Nat. Mater. (2006) 10.1038/nmat1612

[30]

Lim E. J. Polym. Sci., Part A: Polym. Chem. (2006) 10.1002/pola.21586

[31]

Bao Z. Appl. Phys. Lett. (1996) 10.1063/1.117834

[32]

Umeda T. J. Appl. Phys. (2007) 10.1063/1.2711780

[33]

Heeney M. J. Am. Chem. Soc. (2005) 10.1021/ja043112p

[34]

Semiconductors for organic transistors

Antonio Facchetti

Materials Today 2007 10.1016/s1369-7021(07)70017-2

[35]

Newman C. R. Chem. Mater. (2004) 10.1021/cm049391x

[36]

Bao Z. N. J. Mater. Chem. (1999) 10.1039/a902652e

[37]

Gunes S. Chem. Rev. (2007) 10.1021/cr050149z

[38]

Synthetic Principles for Bandgap Control in Linear π-Conjugated Systems

Jean Roncali

Chemical Reviews 1997 10.1021/cr950257t

[39]

A brief history of the development of organic and polymeric photovoltaics

Holger Spanggaard, Frederik C. Krebs

Solar Energy Materials and Solar Cells 2004 10.1016/j.solmat.2004.02.021

[40]

Huitema H. E. A. Nature (2001) 10.1038/414599a

[41]

Babel A. J. Am. Chem. Soc. (2003) 10.1021/ja0371810

[42]

A High-Mobility Electron-Transport Polymer with Broad Absorption and Its Use in Field-Effect Transistors and All-Polymer Solar Cells

Xiaowei Zhan, Zhan'ao Tan, Benoit Domercq et al.

Journal of the American Chemical Society 2007 10.1021/ja071760d

[43]

Chua L. L. Nature (2005) 10.1038/nature03376

[44]

High Electron Mobility in Solution-Cast and Vapor-Deposited Phenacyl−Quaterthiophene-Based Field-Effect Transistors: Toward N-Type Polythiophenes

Joseph A. Letizia, Antonio Facchetti, Charlotte L. Stern et al.

Journal of the American Chemical Society 2005 10.1021/ja054276o

[45]

Janietz S. Macromol. Chem. Phys. (2004) 10.1002/macp.200400095

[46]

Lim E. Macromolecules (2005) 10.1021/ma048128e

[47]

Yoon M. H. J. Am. Chem. Soc. (2006) 10.1021/ja063290d

[48]

Pomerantz M. Tetrahedron Lett. (2003) 10.1016/s0040-4039(03)00016-9

[49]

Zhang Q. T. J. Am. Chem. Soc. (1997) 10.1021/ja964223u

[50]

Zhang Q. T. J. Am. Chem. Soc. (1997) 10.1021/ja9640399

Showing 50 of 91 references

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Details

Published: Jul 01, 2008
Vol/Issue: 130(30)
Pages: 9679-9694

Authors

J

Joseph A. Letizia