Synthesis and characterization of high molecular weight phthalocyanine-PPV copolymers through post-polymerization functionalization

Juan-Jose Cid; Jan Duchateau; Ineke Van Severen; Carolina R. Ganivet; Gema de la Torre; Purificacion Vazquez; Thomas Cleij; Laurence Lutsen; Dirk Vanderzande; Tomas Torres

doi:10.1142/S1088424611003562

Synthesis and characterization of high molecular weight phthalocyanine-PPV copolymers through post-polymerization functionalization

Juan-Jose Cid, Jan Duchateau, Ineke Van Severen, Carolina R. Ganivet, Gema de la Torre, Purificacion Vazquez, Thomas Cleij, Laurence Lutsen, Dirk Vanderzande, Tomas Torres^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

2 Citations (Web of Science)

Abstract

High molecular weight poly(p-phenylenenevinylene) PPV copolymers laterally substituted with zinc (II) phthalocyanines ( Zn(II)Pc -PPV 1 and 2) have been synthesized by means of post-polymerization functionalization reactions through DCC-mediated esterifications between hydroxy-phthalocyanines 4 and 6 and carboxy-bearer PPV copolymers, comprising 2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylenevinylene (MDMO-PPV) and 1,4-(2-(5-carboxypentyloxy)-5-methoxyphenylenevinylene (CPM-PPV) units in a 9:1 (3) and 1:1 (5) ratio, respectively. The resulting copolymer 1 contains a 7 mol % of Pc molecules, while copolymer 2, which is isolated as the soluble fraction of the reaction with the starting 1:1 copolymer (namely having around 50% of COOH -containing monomeric units), holds a 9 mol % of zinc(II) phthalocyanines. 1 and 2 were fully characterized by 1 H NMR, UV-vis and FT-IR spectroscopies.

Original language	English
Pages (from-to)	659-666
Journal	Journal of Porphyrins and Phthalocyanines
Volume	15
Issue number	7-8
DOIs	https://doi.org/10.1142/S1088424611003562
Publication status	Published - 2011
Externally published	Yes

Keywords

conjugated polymers
poly(p-phenylenevinylene)
phthalocyanines
covalent functionalization

Access to Document

10.1142/S1088424611003562

Cite this

Cid, J-J., Duchateau, J., Van Severen, I., Ganivet, C. R., de la Torre, G., Vazquez, P., Cleij, T., Lutsen, L., Vanderzande, D., & Torres, T. (2011). Synthesis and characterization of high molecular weight phthalocyanine-PPV copolymers through post-polymerization functionalization. Journal of Porphyrins and Phthalocyanines, 15(7-8), 659-666. https://doi.org/10.1142/S1088424611003562

@article{59a9c95384bd480fb368c84133a45841,

title = "Synthesis and characterization of high molecular weight phthalocyanine-PPV copolymers through post-polymerization functionalization",

abstract = "High molecular weight poly(p-phenylenenevinylene) PPV copolymers laterally substituted with zinc (II) phthalocyanines ( Zn(II)Pc -PPV 1 and 2) have been synthesized by means of post-polymerization functionalization reactions through DCC-mediated esterifications between hydroxy-phthalocyanines 4 and 6 and carboxy-bearer PPV copolymers, comprising 2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylenevinylene (MDMO-PPV) and 1,4-(2-(5-carboxypentyloxy)-5-methoxyphenylenevinylene (CPM-PPV) units in a 9:1 (3) and 1:1 (5) ratio, respectively. The resulting copolymer 1 contains a 7 mol % of Pc molecules, while copolymer 2, which is isolated as the soluble fraction of the reaction with the starting 1:1 copolymer (namely having around 50% of COOH -containing monomeric units), holds a 9 mol % of zinc(II) phthalocyanines. 1 and 2 were fully characterized by 1 H NMR, UV-vis and FT-IR spectroscopies.",

keywords = "conjugated polymers, poly(p-phenylenevinylene), phthalocyanines, covalent functionalization",

author = "Juan-Jose Cid and Jan Duchateau and {Van Severen}, Ineke and Ganivet, {Carolina R.} and {de la Torre}, Gema and Purificacion Vazquez and Thomas Cleij and Laurence Lutsen and Dirk Vanderzande and Tomas Torres",

year = "2011",

doi = "10.1142/S1088424611003562",

language = "English",

volume = "15",

pages = "659--666",

journal = "Journal of Porphyrins and Phthalocyanines",

issn = "1088-4246",

publisher = "Society of Porphyrins and Phthalocyanines (SPP)",

number = "7-8",

}

Cid, J-J, Duchateau, J, Van Severen, I, Ganivet, CR, de la Torre, G, Vazquez, P, Cleij, T, Lutsen, L, Vanderzande, D & Torres, T 2011, 'Synthesis and characterization of high molecular weight phthalocyanine-PPV copolymers through post-polymerization functionalization', Journal of Porphyrins and Phthalocyanines, vol. 15, no. 7-8, pp. 659-666. https://doi.org/10.1142/S1088424611003562

TY - JOUR

T1 - Synthesis and characterization of high molecular weight phthalocyanine-PPV copolymers through post-polymerization functionalization

AU - Cid, Juan-Jose

AU - Duchateau, Jan

AU - Van Severen, Ineke

AU - Ganivet, Carolina R.

AU - de la Torre, Gema

AU - Vazquez, Purificacion

AU - Cleij, Thomas

AU - Lutsen, Laurence

AU - Vanderzande, Dirk

AU - Torres, Tomas

PY - 2011

Y1 - 2011

N2 - High molecular weight poly(p-phenylenenevinylene) PPV copolymers laterally substituted with zinc (II) phthalocyanines ( Zn(II)Pc -PPV 1 and 2) have been synthesized by means of post-polymerization functionalization reactions through DCC-mediated esterifications between hydroxy-phthalocyanines 4 and 6 and carboxy-bearer PPV copolymers, comprising 2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylenevinylene (MDMO-PPV) and 1,4-(2-(5-carboxypentyloxy)-5-methoxyphenylenevinylene (CPM-PPV) units in a 9:1 (3) and 1:1 (5) ratio, respectively. The resulting copolymer 1 contains a 7 mol % of Pc molecules, while copolymer 2, which is isolated as the soluble fraction of the reaction with the starting 1:1 copolymer (namely having around 50% of COOH -containing monomeric units), holds a 9 mol % of zinc(II) phthalocyanines. 1 and 2 were fully characterized by 1 H NMR, UV-vis and FT-IR spectroscopies.

AB - High molecular weight poly(p-phenylenenevinylene) PPV copolymers laterally substituted with zinc (II) phthalocyanines ( Zn(II)Pc -PPV 1 and 2) have been synthesized by means of post-polymerization functionalization reactions through DCC-mediated esterifications between hydroxy-phthalocyanines 4 and 6 and carboxy-bearer PPV copolymers, comprising 2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylenevinylene (MDMO-PPV) and 1,4-(2-(5-carboxypentyloxy)-5-methoxyphenylenevinylene (CPM-PPV) units in a 9:1 (3) and 1:1 (5) ratio, respectively. The resulting copolymer 1 contains a 7 mol % of Pc molecules, while copolymer 2, which is isolated as the soluble fraction of the reaction with the starting 1:1 copolymer (namely having around 50% of COOH -containing monomeric units), holds a 9 mol % of zinc(II) phthalocyanines. 1 and 2 were fully characterized by 1 H NMR, UV-vis and FT-IR spectroscopies.

KW - conjugated polymers

KW - poly(p-phenylenevinylene)

KW - phthalocyanines

KW - covalent functionalization

U2 - 10.1142/S1088424611003562

DO - 10.1142/S1088424611003562

M3 - Article

SN - 1088-4246

VL - 15

SP - 659

EP - 666

JO - Journal of Porphyrins and Phthalocyanines

JF - Journal of Porphyrins and Phthalocyanines

IS - 7-8

ER -