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Peripheral Substitution of a Near-IR-Absorbing Soluble Phthalocyanine Using “Click” Chemistry

Journal Article · · Chemistry - A European Journal
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A series of near-IR-absorbing soluble phthalocyanines (Pcs) with eight alkyne moieties as side chains of the chromophore have been synthesized. One of these Pcs has been used as a scaffold for functional group modification using alkyne–azide click chemistry with various azides. This led to a small library of Pcs with photo and thermal crosslinkable, dendritic, and hydrophilic moieties starting from a single Pc molecule. A patterned thin film was fabricated by photocrosslinking one of these Pc derivatives.

Research Organization:
Energy Frontier Research Centers (EFRC) (United States). Center for Interface Science: Solar Electric Materials (CISSEM)
Sponsoring Organization:
USDOE SC Office of Basic Energy Sciences (SC-22)
DOE Contract Number:
SC0001084
OSTI ID:
1380677
Journal Information:
Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 30 Vol. 17; ISSN 0947-6539
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English

References (17)

Modification of Symmetrically Substituted Phthalocyanines Using Click Chemistry: Phthalocyanine Nanostructures by Nanoimprint Lithography journal August 2009
Click-Chemie: diverse chemische Funktionalität mit einer Handvoll guter Reaktionen journal June 2001
A Novel Potent Nicotinamide Phosphoribosyltransferase Inhibitor Synthesized via Click Chemistry journal January 2010
Synthesis and aggregation behavior of hosts containing phthalocyanine and crown ether subunits journal July 1987
Efficient Sensitization of Nanocrystalline TiO2 Films by a Near-IR-Absorbing Unsymmetrical Zinc Phthalocyanine journal January 2007
Phthalocyanines: From outstanding electronic properties to emerging applications journal January 2008
Solution and Thin-Film Aggregation Studies of Octasubstituted Dendritic Phthalocyanines journal May 2009
Organic photoconductive materials: recent trends and developments journal January 1993
Self-Assembly of Disk-Shaped Molecules to Coiled-Coil Aggregates with Tunable Helicity journal April 1999
Non-aggregating octasubstituted dendritic phthalocyanines journal April 2003
Phthalocyanines: The Need for Selective Synthetic Approaches journal August 2000
Click Chemistry: Diverse Chemical Function from a Few Good Reactions journal June 2001
Effect of Peripheral Substitution on the Electronic Absorption and Fluorescence Spectra of Metal-Free and Zinc Phthalocyanines journal October 2003
Organic field‐effect transistors with high mobility based on copper phthalocyanine journal November 1996
A Novel Modular Approach to Triazole-Functionalized Phthalocyanines Using Click Chemistry journal January 2009
Organic Photovoltaic Cells Based On Solvent-Annealed, Textured Titanyl Phthalocyanine/C60 Heterojunctions journal June 2009
Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromolecules journal October 1990

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