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.
Bibliographical noteFunding Information:
T.M.P. acknowledges the following: (i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research and the UMM Division of Science and Mathematics for financial assistance, and (ii) a Grant-in-Aid of Research, Artistry and Scholarship from the Office of the Dean of the Graduate School and the Supercomputing Institute of the University of Minnesota. T.M.P. and D.E.J. acknowledge the National Science Foundation Major Research Instrumentation Award #1125975 for funding the acquisition of the X-ray diffractometer used for data collection in this investigation. A.B. and T.M.P. acknowledge the Undergraduate Research Opportunities Program (UROP) of the University of Minnesota.
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- Organic materials synthesis
- Thermolabile materials X-ray structure analysis