Synthesis and characterization of naphthalene diimide/diethynylbenzene copolymers

Tissa Sajoto, Shree Prakash Tiwari, Huifang Li, Chad Risko, Stephen Barlow, Qing Zhang, Jian Yang Cho, Jean Luc Brédas, Bernard Kippelen, Seth R. Marder*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

25 Scopus citations


A series of conjugated polymers has been synthesized by Sonogashira coupling of N,N′-bis(2-octyldodecyl)-2,6-dibromonaphthalene-1,4,5,8- bis(dicarboximide) and four para-diethynylbenzene derivatives: 1,4-diethynyl-2,5-dihexadecyloxybenzene, 1,4-diethynyl-2,5-bis(2- octyldodecyloxy) benzene, 1,4-bis(2-ethylhexyl)-2,5-diethynylbenzene, 1,4-diethynyl-2,5-bis(trifluoromethyl)benzene. The polymers display absorption maxima at wavelengths ranging from 530 nm to 654 nm with molar absorptivities ranging from ca. 4 to 7 × 104 M-1 cm-1. The peak reduction potentials, determined by differential pulse voltammetry, for polymer films varied from -0.93 to -1.14 V vs. ferrocenium/ferrocene with the trifluoromethyl-substituted derivative being the most readily reduced. All four polymers exhibited electron transport characteristics in bottom-gate/top-contact field-effect transistors, showing average electron mobility values ranging from 1.4 × 10-4 to 3.7 × 10-3 cm2 V-1 s-1.

Original languageEnglish (US)
Pages (from-to)1072-1078
Number of pages7
Issue number5
StatePublished - Feb 28 2012
Externally publishedYes

Bibliographical note

Funding Information:
We would like to acknowledge Benjamin Wunsch, Chun Huang, and Sergio Paniagua for acquiring TGA and DSC data. This work was funded by Solvay S.A., the Office of Naval Research , and the STC Program of the National Science Foundation ( DMR-0120967 ).


  • Conjugated polymers
  • Electron transport
  • Naphthalene diimide polymers

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry


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