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Characterization of the porous nature of a phthalocyanine derivative with axial ligation designed to prevent aggregation

Carl A. Barker

Department of Chemistry, Durham University, South Road, Durham DH1 3LE, United Kingdom

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Alan Massey

Department of Chemistry, Durham University, South Road, Durham DH1 3LE, United Kingdom

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Aidan Rhodes

Department of Chemistry, Durham University, South Road, Durham DH1 3LE, United Kingdom

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Martin R. Bryce

Department of Chemistry, Durham University, South Road, Durham DH1 3LE, United Kingdom

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, and

Ritu Kataky

Department of Chemistry, Durham University, South Road, Durham DH1 3LE, United Kingdom

Corresponding author, tel: +44 (0)3342091, fax: +44 (0)3844737.

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https://doi.org/10.1142/S1088424610002173Cited by:0 (Source: Crossref)

Abstract

Judiciously designed phthalocyanines (Pcs), such as silicon-Pc bis(3,5-diphenyl)benzoate (1c), with axial substituents which prevent aggregation, can self-assemble to form ordered nanoporous films on electrode surfaces. In this paper, complementary techniques such as Scanning Kelvin Nanoprobe (SKN) microscopy, Atom Force Microscopy (AFM) and electrochemical measurements are used to demonstrate that films formed by silicon-Pc bis(3,5-diphenyl)benzoate allow size- and charge- selective transport of probe molecules through well-defined intermolecular cavities. In contrast, the analogs silicon-Pc bis(4-tert-butylbenzoate) (1a) and silicon-Pc bis(3-thienyl)acetate (1b) have different film morphologies when solvent-cast in the same manner and block the electrode surface. The role of the different axial substituents in orienting the molecules on the substrate is discussed.

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