Synthesis, characterization, and electronic properties of a thermally-labile isoindigo

Ted M. Pappenfus, Abdala Bashir, Blake J. Gerold, Paul M. Granaas, Daron E. Janzen

Research output: Contribution to journalArticlepeer-review

1 Scopus citations


Addition of tert-butoxycarbonyl (Boc) groups to 6,6′-dibromoisoindigo (3a) provides a highly soluble material that displays π-stacking in the solid state as evidenced by a single crystal X-ray study. This Boc-substituted molecule (3b) was compared to an alkyl-substituted isoindigo using techniques such as TGA, UV-Vis and cyclic voltammetry. TGA analysis reveals the thermolabile Boc groups of 3b can be removed at elevated temperatures to afford the parent isoindigo. Electrochemical analyses, in conjunction with density functional theory (DFT) calculations, reveals enhanced electron affinities of 3b relative to alkyl-substituted isoindigos.

Original languageEnglish (US)
Pages (from-to)96-99
Number of pages4
JournalJournal of Molecular Structure
StatePublished - Apr 28 2015

Bibliographical note

Publisher Copyright:
© 2015 Elsevier B.V. All rights reserved.


  • Isoindigo
  • Organic materials synthesis
  • Thermolabile materials X-ray structure analysis


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