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Issue 10, 2015
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A push–pull unsymmetrical subphthalocyanine dimer

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Abstract

Unsymmetrical subphthalocyanine fused dimers have been prepared from appropriate ortho-dinitrile SubPc precursors. In particular, either electron-donating or electron-accepting substituents have been introduced on each SubPc constituent unit, resulting in unprecedented push–pull π-extended curved aromatic macrocycles. From fluorescence experiments in solvents of different polarity we conclude a dual fluorescence, namely a delocalized singlet excited state (1.73 eV) and a polarized charge transfer state (<1.7 eV). Pump probe experiments corroborate the dual nature of the fluorescence. On one hand, the delocalized singlet excited state gives rise to a several nanosecond lasting intersystem crossing yielding the corresponding triplet excited state. On the other hand, the polarized charge transfer state deactivates within a few picosesonds. Visualization of the charge transfer state was accomplished by means of molecular modeling with a slight polarization of the HOMO towards the electron donor and of the LUMO towards the electron acceptor.

Graphical abstract: A push–pull unsymmetrical subphthalocyanine dimer

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Publication details

The article was received on 10 May 2015, accepted on 16 Jun 2015 and first published on 17 Jun 2015


Article type: Edge Article
DOI: 10.1039/C5SC01709B
Citation: Chem. Sci., 2015,6, 5571-5577
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    A push–pull unsymmetrical subphthalocyanine dimer

    G. Zango, J. Zirzlmeier, C. G. Claessens, T. Clark, M. V. Martínez-Díaz, D. M. Guldi and T. Torres, Chem. Sci., 2015, 6, 5571
    DOI: 10.1039/C5SC01709B

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