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Issue 2, 2015
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Ultrafast photoinduced electron transfer in face-to-face charge-transfer π-complexes of planar porphyrins and hexaazatriphenylene derivatives

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Abstract

Charge-transfer (CT) π-complexes are formed between planar porphyrins and 1,4,5,8,9,12-hexaazatriphenylene (HAT) derivatives with large formation constants (e.g., 104 M−1), exhibiting broad CT absorption bands. The unusually large formation constants result from close face-to-face contact between two planar π-planes of porphyrins and HAT derivatives. The redox potentials of porphyrins and HAT derivatives measured by cyclic voltammetry indicate that porphyrins and HAT derivatives act as electron donors and acceptors, respectively. The formation of 1 : 1 CT complexes between porphyrins and HAT derivatives was examined by UV-vis, fluorescence and 1H NMR measurements in nonpolar solvents. The occurrence of unprecedented ultrafast photoinduced electron transfer from the porphyrin unit to the HAT unit in the CT π-complex was observed by femtosecond laser flash photolysis measurements. A highly linear aggregate composed of a planar porphyrin and an HAT derivative was observed by transmission electron microscopy (TEM) and atomic force microscopy (AFM).

Graphical abstract: Ultrafast photoinduced electron transfer in face-to-face charge-transfer π-complexes of planar porphyrins and hexaazatriphenylene derivatives

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Publication details

The article was received on 10 Sep 2014, accepted on 28 Nov 2014 and first published on 28 Nov 2014


Article type: Edge Article
DOI: 10.1039/C4SC02787F
Citation: Chem. Sci., 2015,6, 1498-1509
  • Open access: Creative Commons BY-NC license
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    Ultrafast photoinduced electron transfer in face-to-face charge-transfer π-complexes of planar porphyrins and hexaazatriphenylene derivatives

    T. Aoki, H. Sakai, K. Ohkubo, T. Sakanoue, T. Takenobu, S. Fukuzumi and T. Hasobe, Chem. Sci., 2015, 6, 1498
    DOI: 10.1039/C4SC02787F

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