Hostname: page-component-78c5997874-ndw9j Total loading time: 0 Render date: 2024-11-17T21:27:36.271Z Has data issue: false hasContentIssue false
  • English
  • Français

Length-dependent self-assembly of oligothiophene derivatives in thin films

Published online by Cambridge University Press:  19 January 2011

Brian S. Rolczynski ,
Jodi M. Szarko ,
Byeongdu Lee ,
Joseph Strzalka ,
Jianchang Guo ,
Yongye Liang ,
Luping Yu  and
Lin X. Chen
Brian S. Rolczynski
Affiliation:
Department of Chemistry, Northwestern University, Evanston, Illinois 60208; Chemical Sciences and Engineering Division and Argonne National Laboratory, Argonne, Illinois 60439; and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208
Jodi M. Szarko
Affiliation:
Department of Chemistry, Northwestern University, Evanston, Illinois 60208; and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208
Byeongdu Lee
Affiliation:
X-ray Sciences Division, Argonne National Laboratory, Argonne, Illinois 60439
Joseph Strzalka
Affiliation:
X-ray Sciences Division, Argonne National Laboratory, Argonne, Illinois 60439
Jianchang Guo
Affiliation:
Chemical Sciences and Engineering Division and Argonne National Laboratory, Argonne, Illinois 60439; and Department of Chemistry and The James Franck Institute, The University of Chicago, Chicago, Illinois 60637
Yongye Liang
Affiliation:
Department of Chemistry and The James Franck Institute, The University of Chicago, Chicago, Illinois 60637
Luping Yu*
Affiliation:
Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208; and Department of Chemistry and The James Franck Institute, The University of Chicago, Chicago, Illinois 60637
Lin X. Chen*
Affiliation:
Department of Chemistry, Northwestern University, Evanston, Illinois 60208; Chemical Sciences and Engineering Division and Argonne National Laboratory, Argonne, Illinois 60439; and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois 60208
*
a)Address all correspondence to these authors. e-mail: [email protected]
b)e-mail: [email protected]
Get access

Abstract

Thin-film aggregation characteristics of a series of oligothiophenes with a central thieno[3,4-b]thiophene ester unit and 4 (M5), 8 (M9), and 16 (M17) regioregular hexylthiophene units were investigated. These oligomers exhibited length-dependent self-assembly characteristics upon spin coating. M9 formed long fibers, while M5 and M17 formed random domains. Grazing incidence x-ray diffraction was performed to understand the reason for this length dependence. The M5 had a dominant ester–ester interaction that disrupted long-range order. The M9 morphology was due to a balance of orthogonal backbone and ester effects, which imposed long-range order on the M9 aggregates. Meanwhile, the M17 ester chain had a smaller relative contribution to packing and functioned as a molecular defect, disrupting long-range order. As a result, though the local self-assembly between monomers was very similar for the molecules, backbone length dependent changes in intermolecular forces dominated long-range structure. The analysis of self-assembly characteristics in these materials provides guidance in the design of organic conjugated materials for use in semiconductor devices.

Keywords

X-ray Diffraction (XRD)Self-AssemblyPolymer
Type
Reviews
Information
Journal of Materials Research , Volume 26 , Issue 2: Focus Issue: Self-Assembly and Directed Assembly of Advanced Materials , 28 January 2011 , pp. 296 - 305
Copyright
Copyright © Materials Research Society 2011

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

1.Liang, Y., Feng, D., Guo, J., Szarko, J.M., Ray, C., Chen, L.X., and Yu, L.: Regioregular oligomer and polymer containing thieno[3,4-b]thiophene moiety for efficient organic solar cells. Macromolec. 42, 1091 (2009).CrossRefGoogle Scholar
2.Dennler, G., Scharber, M., and Brabec, C.: Polymer-fullerene bulk-heterojunction solar cells. Adv. Mater. 27, 1 (2009).Google Scholar
3.Holdcroft, S.: Patterning π-conjugated polymers. Adv. Mater. 13, 7154 (2001).3.0.CO;2-2>CrossRefGoogle Scholar
4.Friend, R.H., Gymer, R.W., Holmes, A.B., Burroughes, J.H., Marks, R.N., Taliani, C., Bradley, D., Santos, D.A.D., Brédas, J.L., Lögdlund, M., and Salaneck, W.R.: Electroluminescence in conjugated polymers. Nature 397, 121 (1999).CrossRefGoogle Scholar
5.Mayer, A.C., Toney, M.F., Scully, S.R., Rivnay, J., Brabec, C., Scharber, M., Koppe, M., McCulloch, M.H., and McGehee, M.D.: Bimolecular crystals of fullerenes in conjugated polymers and the implications of molecular mixing for solar cells. Adv. Funct. Mater. 19, 1173 (2009).CrossRefGoogle Scholar
6.Desiraju, G.R.: Crystal engineering: A holistic view. Angew. Chem. 46, 8342 (2007).CrossRefGoogle ScholarPubMed
7.Etter, M.C.: Encoding and decoding hydrogen-bond patterns of organic compounds. Acc. Chem. Res. 23, 120 (1990).CrossRefGoogle Scholar
8.Gavezzotti, A.: Molecular Aggregation: Structure Analysis and Molecular Simulation of Crystals and Liquids (Oxford University Press, New York, NY, 2007), pp. 367–418.Google Scholar
9.Israelachvili, J.N.: Intermolecular and Surface Forces (Academic Press, San Diego, CA, 1995).Google Scholar
10.Dante, M., Peet, J., and Nguyen, T.: Nanoscale charge transport and internal structure of bulk heterojunction conjugated polymer/fullerene solar cells by scanning-probe microscopy. J. Phys. Chem. C 112, 7241 (2008).CrossRefGoogle Scholar
11.Pingree, L., Reid, O.G., and Ginger, D.: Electrical scanning-probe microscopy on active organic electronic devices. Adv. Mater. 21, 19 (2009).CrossRefGoogle Scholar
12.Peet, J., Kim, J.Y., Coates, N.E., Ma, W.L., Moses, D., Heeger, A.J., and Bazan, G.C.: Efficiency enhancement in low-bandgap polymer solar cells by processing with alkane dithiols. Nat. Mater. 6, 497 (2007).CrossRefGoogle ScholarPubMed
13.Hwang, I., Moses, D., and Heeger, A.: Photoinduced carrier generation in P3HT/PCBM bulk heterojunction materials. J. Phys. Chem. C 112, 4350 (2008).CrossRefGoogle Scholar
14.Winokur, M.J., Spiegel, D., Kim, Y., Hotta, S., and Heeger, A.J.: Structural and absorption studies of the thermochromic transition in poly(3-hexylthiophene). Synth. Met. 28, C419 (1989).CrossRefGoogle Scholar
15.Gavezzotti, A. and Filippini, G.: Crystal packing and lattice energies of polythienyls: Calculations and predictions. Synth. Met. 40, 257 (1991).CrossRefGoogle Scholar
16.Azumi, R., Goto, M., Honda, K., and Matsumoto, M.: Conformation and packing of odd-numbered alpha-oligothiophenes in single crystals. Bull. Chem. Soc. Jpn. 76, 1561 (2003).CrossRefGoogle Scholar
17.Cornil, J., Beljonne, D., Calbert, J., and Brédas, J.: Interchain interactions in organic p-conjugated materials: Impact on electronic structure, optical response, and charge transport. Adv. Mater. 13, 1053 (2001).3.0.CO;2-7>CrossRefGoogle Scholar
18.Fichou, D.: Structural order in conjugated oligothiophenes and its implications on opto-electronic devices. J. Mater. Chem. 10, 571 (2000).CrossRefGoogle Scholar
19.Lehn, J.: Toward self-organization and complex matter. Science 295, 2400 (2002).CrossRefGoogle ScholarPubMed
20.Schenning, A. and Meijer, E.: Supramolecular electronics: Nanowires from self-assembled π-conjugated systems. Chem. Commun. 3245 (2005).CrossRefGoogle ScholarPubMed
21.Guo, J., Liang, Y., Szarko, J., Lee, B., Son, H.J., Rolczynski, B.S., Yu, L., and Chen, L.X.: Structure, dynamics, and power conversion efficiency correlations in a new low bandgap polymer: PCBM solar cell. J. Phys. Chem. B 114, 742 (2010).CrossRefGoogle Scholar
22.Szarko, J.M., Rolczynski, B.S., Guo, J., Liang, Y., He, F., Mara, M.W., Yu, L., and Chen, L.X.: Electronic processes in conjugated diblock oligomers mimicking low band-gap polymers: Experimental and theoretical spectral analysis. J. Phys. Chem. B 114, 14505 (2010).CrossRefGoogle ScholarPubMed
23.Beljonne, D., Shuai, Z., Pourtois, G., and Bredas, J.L.: Spin-orbit coupling and intersystem crossing in conjugated polymers: A configuration interaction description. J. Phys. Chem. A 105, 3899 (2001).CrossRefGoogle Scholar
24.Chabinyc, M.: X-ray scattering from films of semiconducting polymers. Pol. Rev. 48, 463 (2008).CrossRefGoogle Scholar
25.Kim, Y., Cook, S., Tuladhar, S.M., Choulis, S.A., Nelson, J., Durrant, J.R., Bradley, D.D.C., Giles, M., McCulloch, I., Ha, C-s., and Ree, M.: A strong regioregularity effect in self-organizing conjugated polymer films and high-efficiency polythiophene: Fullerene solar cells. Nat. Mater. 5, 198 (2006).CrossRefGoogle Scholar
26.Joshi, S., Grigorian, S., and Pietsch, U.: X-ray structural and crystallinity studies of low and high molecular weight poly(3-hexylthiophene). Phys. Status Solidi, A Appl. Mater. Sci. 205, 488 (2008).CrossRefGoogle Scholar
27.Raudino, A. and Pignataro, B.: Supra-aggregates of fiber-forming anisotropic molecules. J. Phys. Chem. B 110, 2116 (2006).CrossRefGoogle ScholarPubMed