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

Research output: Contribution to journalArticle

41 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)13840-13843
Number of pages4
JournalJournal of the American Chemical Society
Volume131
Issue number38
DOIs
StatePublished - 2009

Fingerprint

Click Chemistry
Nanoimprint lithography
Nanostructures
Cinnamates
Derivatives
Organic field effect transistors
Fabrication
Photodynamic therapy
Alkynes
Azides
Cycloaddition
Cycloaddition Reaction
Photochemotherapy
Functional groups
Copper
Technology
Equipment and Supplies
Processing
phthalocyanine

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

@article{289848eed9b642278fcf11bea119f116,
title = "Modification of symmetrically substituted phthalocyanines using click chemistry: Phthalocyanine nanostructures by nanoimprint lithography",
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.",
author = "Xiaochun Chen and Jayan Thomas and Palash Gangopadhyay and Norwood, {Robert A} and Peyghambarian, {Nasser N} and Mcgrath, {Dominic V}",
year = "2009",
doi = "10.1021/ja905683g",
language = "English (US)",
volume = "131",
pages = "13840--13843",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "38",

}

TY - JOUR

T1 - Modification of symmetrically substituted phthalocyanines using click chemistry

T2 - Phthalocyanine nanostructures by nanoimprint lithography

AU - Chen, Xiaochun

AU - Thomas, Jayan

AU - Gangopadhyay, Palash

AU - Norwood, Robert A

AU - Peyghambarian, Nasser N

AU - Mcgrath, Dominic V

PY - 2009

Y1 - 2009

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=70349731651&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70349731651&partnerID=8YFLogxK

U2 - 10.1021/ja905683g

DO - 10.1021/ja905683g

M3 - Article

C2 - 19772367

AN - SCOPUS:70349731651

VL - 131

SP - 13840

EP - 13843

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 38

ER -