Reactions between 3,4-propylenedioxythiophenes (ProDOTs) and N-alkyl isatins under ambient conditions result in isomerically pure indophenine materials as confirmed by TLC and 1H NMR analysis. The resulting low band gap materials exhibit favorable inter- A nd intramolecular interactions, high thermal stabilities, low energy electronic transitions, and amphoteric redox behavior.
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; (iii) the Howard Hughes Medical Institute (HHMI) Pathways to Science Program for financial assistance; and (iv) Dr. Bryan Nell for assistance with the NMR experiments. T.M.P. and D.E.J. acknowledge the National Science Foundation Major Research Instrumentation Award No. 1125975 for funding the acquisition of the X-ray diffractometer used for data collection in this investigation.