Physicochemical Characterization of Subporphyrazines—Lower Subphthalocyanine Homologues

Authors

  • G. M. Aminur Rahman Dr.,

    1. Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany), Fax: (+49) 9131-8528307
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  • Daniela Lüders,

    1. Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany), Fax: (+49) 9131-8528307
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  • M. Salomé Rodríguez-Morgade Dr.,

    1. Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain), Fax: (+34) 914-973-966
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  • Esmeralda Caballero Dr.,

    1. Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain), Fax: (+34) 914-973-966
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  • Tomás Torres Prof.,

    1. Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain), Fax: (+34) 914-973-966
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  • Dirk M. Guldi Prof. Dr.

    1. Department of Chemistry and Pharmacy & Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany), Fax: (+49) 9131-8528307
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Abstract

The periphery is central: The luminescent properties of boron(III) subporphyrazines are strongly influenced by their peripheral functionalization. These photoactive materials generate long-lived triplet excited states that mediate the sensitized production of singlet oxygen. Furthermore, their ability to behave either as oxidizing or reducing chromophores is promising for their application in molecular photovoltaics.

original image

Physicochemical characterization of boron(III) subporphyrazines (SubPzs)—lower subphthalocyanine (SubPc) homologues—has been carried out for the first time. The SubPz macrocycle can act both as an oxidizing and a reducing entity, giving rise to stable radical anion or radical cation species, respectively. SubPzs are luminescent and exhibit fluorescence quantum yields that are in the range known for SubPcs. The peripheral substitution plays a dramatic role with respect to the luminescence properties. Moreover, as with SubPcs, deactivation of the singlet excited state of the SubPzs by intersystem crossing affords long-lived triplet excited states, which are amenable to being used as singlet-oxygen generators. Subporphyrazines are also promising electro- and photoactive materials for molecular photovoltaics.

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