Influence of Annelation on the Electronic Properties of Phthalocyanine Macrocycles

E. Ortí; M. C. Piqueras; R. Crespo; J. L. Brédas

doi:10.1021/cm00008a009

Influence of Annelation on the Electronic Properties of Phthalocyanine Macrocycles

E. Ortí, M. C. Piqueras, R. Crespo, J. L. Brédas

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92 Scopus citations

Abstract

Service de Chimie des Matériaux Nouveaux et Département des Matériaux et Procédés, Université de Mons, Avenue Maistriau, 21, B-7000 Mons, Belgium We present the results of valence effective Hamiltonian (VEH) nonempirical pseudopotential calculations on the electronic structure of various macrocycles including tetraazaporphyrin, phthalocyanine, 2,3-naphthalocyanine, 1,2-naphthalocyanine, and phenanthrenocyanine. We focus our attention on the evolution of the oxidation potentials and lowest optical absorptions as a function of linear or angular annelation of benzene rings onto the basic tetraazaporphyrin macrocycle. The VEH results are found to agree with cyclic voltammetry and optical absorption experimental data. These results provide a coherent picture of the evolution of the electrical conductivity properties in crystals and polymers derived from those compounds.

Original language	English (US)
Pages (from-to)	110-116
Number of pages	7
Journal	Chemistry of Materials
Volume	2
Issue number	2
DOIs	https://doi.org/10.1021/cm00008a009
State	Published - Mar 1 1990
Externally published	Yes

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
Materials Chemistry

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10.1021/cm00008a009

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title = "Influence of Annelation on the Electronic Properties of Phthalocyanine Macrocycles",

abstract = "Service de Chimie des Mat{\'e}riaux Nouveaux et D{\'e}partement des Mat{\'e}riaux et Proc{\'e}d{\'e}s, Universit{\'e} de Mons, Avenue Maistriau, 21, B-7000 Mons, Belgium We present the results of valence effective Hamiltonian (VEH) nonempirical pseudopotential calculations on the electronic structure of various macrocycles including tetraazaporphyrin, phthalocyanine, 2,3-naphthalocyanine, 1,2-naphthalocyanine, and phenanthrenocyanine. We focus our attention on the evolution of the oxidation potentials and lowest optical absorptions as a function of linear or angular annelation of benzene rings onto the basic tetraazaporphyrin macrocycle. The VEH results are found to agree with cyclic voltammetry and optical absorption experimental data. These results provide a coherent picture of the evolution of the electrical conductivity properties in crystals and polymers derived from those compounds.",

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AU - Ortí, E.

AU - Piqueras, M. C.

AU - Crespo, R.

AU - Brédas, J. L.

PY - 1990/3/1

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N2 - Service de Chimie des Matériaux Nouveaux et Département des Matériaux et Procédés, Université de Mons, Avenue Maistriau, 21, B-7000 Mons, Belgium We present the results of valence effective Hamiltonian (VEH) nonempirical pseudopotential calculations on the electronic structure of various macrocycles including tetraazaporphyrin, phthalocyanine, 2,3-naphthalocyanine, 1,2-naphthalocyanine, and phenanthrenocyanine. We focus our attention on the evolution of the oxidation potentials and lowest optical absorptions as a function of linear or angular annelation of benzene rings onto the basic tetraazaporphyrin macrocycle. The VEH results are found to agree with cyclic voltammetry and optical absorption experimental data. These results provide a coherent picture of the evolution of the electrical conductivity properties in crystals and polymers derived from those compounds.

AB - Service de Chimie des Matériaux Nouveaux et Département des Matériaux et Procédés, Université de Mons, Avenue Maistriau, 21, B-7000 Mons, Belgium We present the results of valence effective Hamiltonian (VEH) nonempirical pseudopotential calculations on the electronic structure of various macrocycles including tetraazaporphyrin, phthalocyanine, 2,3-naphthalocyanine, 1,2-naphthalocyanine, and phenanthrenocyanine. We focus our attention on the evolution of the oxidation potentials and lowest optical absorptions as a function of linear or angular annelation of benzene rings onto the basic tetraazaporphyrin macrocycle. The VEH results are found to agree with cyclic voltammetry and optical absorption experimental data. These results provide a coherent picture of the evolution of the electrical conductivity properties in crystals and polymers derived from those compounds.

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Influence of Annelation on the Electronic Properties of Phthalocyanine Macrocycles

Abstract

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