Modification of symmetrically substituted phthalocyanines using click chemistry: phthalocyanine nanostructures by nanoimprint lithography

Xiaochun Chen; Jayan Thomas; Palash Gangopadhyay; Robert A Norwood; N Peyghambarian; Dominic V McGrath

doi:10.1021/ja905683g

Modification of symmetrically substituted phthalocyanines using click chemistry: phthalocyanine nanostructures by nanoimprint lithography

J Am Chem Soc. 2009 Sep 30;131(38):13840-3. doi: 10.1021/ja905683g.

Authors

Xiaochun Chen¹, Jayan Thomas, Palash Gangopadhyay, Robert A Norwood, N Peyghambarian, Dominic V McGrath

Affiliation

¹ Department of Chemistry and College of Optical Sciences, The University of Arizona, Tucson, Arizona 85721, USA.

PMID: 19772367
DOI: 10.1021/ja905683g

Abstract

Phthalocyanines (Pcs) are commonly applied to advanced technologies such as optical limiting, photodynamic therapy (PDT), organic field-effect transistors (OFETs), and organic photovoltaic (OPV) devices, where they are used as the p-type layer. An approach to Pc structural diversity and the incorporation of a functional group that allows fabrication of solvent resistant Pc nanostructures formed by using a newly developed nanoimprint by melt processing (NIMP) technique, a variant of standard nanoimprint lithography (NIL), is reported. Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), a click chemistry reaction, serves as an approach to structural diversity in Pc macrocycles. We have prepared octaalkynyl Pc 1b and have modified this Pc using the CuAAC reaction to yield four Pc derivatives 5a-5d with different peripheral substituents on the macrocycle. One of these derivatives, 5c, has photo-cross-linkable cinnamate residues, and we have demonstrated the fabrication of robust cross-linked photopatterned and imprinted nanostructures from this material.