Synthesis and study of electrochemical and optical properties of substituted perylenemonoimides in solutions and on solid surfaces

Zafar Ahmed; Lijo George; Arto Hiltunen; Helge Lemmetyinen; Terttu Hukka; Alexander Efimov

doi:10.1039/C5TA02241J

Synthesis and study of electrochemical and optical properties of substituted perylenemonoimides in solutions and on solid surfaces

Zafar Ahmed,^a Lijo George,^a Arto Hiltunen,^a Helge Lemmetyinen,^a Terttu Hukka^a and Alexander Efimov*^a

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* Corresponding authors

^a Department of Chemistry and Bioengineering, Tampere University of Technology, Tampere, Finland
E-mail: alexandre.efimov@tut.fi

Abstract

A new and efficient methodology towards the synthesis of 7-pyrrolidinyl and 7,12-bispyrrolidinyl perylenemonoimide monoanhydrides (PMI monoanhydrides) and their corresponding dicarboxylic acids is devised. The high yields (70–96%) and facile synthesis of PMI monoanhydrides, as compared to traditional methodologies, make the method attractive and versatile. The reported 7,12-bispyrrolidinyl PMI monoanhydrides are a new family of peryleneimides, where both the bay-substituents are located towards the anhydride cycle. The electrochemical and optical properties of target molecules and their precursors were investigated using UV-Vis spectroscopy and differential pulse voltammetry. Atomic charges and electronic properties were calculated using density functional theory (DFT). In addition, self-assembling monolayers of the PMI monoanhydrides and their corresponding diacids were successfully formed over ZnO and TiO₂ films. The results of the current study indicate that these molecules are potentially good candidates for various applications in the fields of organic electronics and solar cells.

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The article was received on 27 Mar 2015, accepted on 13 May 2015 and first published on 13 May 2015

Article type: Paper

DOI: 10.1039/C5TA02241J

Author version available: Download Author version (PDF)

Citation: J. Mater. Chem. A, 2015,3, 13332-13339

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Synthesis and study of electrochemical and optical properties of substituted perylenemonoimides in solutions and on solid surfaces

Z. Ahmed, L. George, A. Hiltunen, H. Lemmetyinen, T. Hukka and A. Efimov, J. Mater. Chem. A, 2015, 3, 13332
DOI: 10.1039/C5TA02241J
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Journal of Materials Chemistry A

Synthesis and study of electrochemical and optical properties of substituted perylenemonoimides in solutions and on solid surfaces

Abstract

Supplementary files

Publication details

Synthesis and study of electrochemical and optical properties of substituted perylenemonoimides in solutions and on solid surfaces

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