Crystal design for organic semicondutors: The effects of substitution on crystal packing

John E. Anthony, Balaji Purushothaman

Research output: Chapter in Book/Report/Conference proceedingConference contributionpeer-review

6 Scopus citations


Electronic devices based on organic materials have been an area of intense research for the past several years. Pentacene, an oligoacene, is regarded as a benchmark due to its high charge carrier mobility. However it has poor solubilty, unoptimized π-overlap and is highly unstable. We have successfully demonstrated that peri-functionalization with trialkylsilyl ethynyl groups enhances the π-stacking, solubility and stability of pentacene and related compounds. TIPS pentacene exhibits both two dimensional (2D) 71-stacking and good solubilty in common organic solvents. However changing the solubilizing groups or functionalizing the acene core results in a disruption of the desired 2D 71-stacking. Molecules with one dimensional (1D) π-stacking have poorer mobility than those with 2D π-stacking and hence larger solubilizing groups are required to change the π-stacking to 2D. The emphasis of this paper is to show how small changes in substitution can disrupt π-stacking in these molecules and how one can achieve the desired π-stacking by careful selection of solubilzing groups.

Original languageEnglish
Title of host publicationOrganic Field-Effect Transistors VI
StatePublished - 2007
EventOrganic Field-Effect Transistors VI - San Diego, CA, United States
Duration: Aug 26 2007Aug 28 2007

Publication series

NameProceedings of SPIE - The International Society for Optical Engineering
ISSN (Print)0277-786X


ConferenceOrganic Field-Effect Transistors VI
Country/TerritoryUnited States
CitySan Diego, CA


  • Anthradithiophene
  • Crystal engineering
  • Pentacene
  • Soluble semiconductor

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics
  • Computer Science Applications
  • Applied Mathematics
  • Electrical and Electronic Engineering


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