Unexpected formation of benziphthalocyanine dimer: An easily synthesizable dimer of phthalocyanine analogue

[Display omitted] •Methylene-bridged benziphthalocyanine dimer was synthesized at room temperature.•Single-crystal X-ray diffraction analysis revealed a V-shaped structure.•The dimer exhibited near-IR absorption and fluorescence. Methylene-bridged benziphthalocyanine dimer 2 was unexpectedly generat...

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Bibliographic Details
Published in:Tetrahedron letters 2017-06, Vol.58 (23), p.2267-2271
Main Authors: Toriumi, Naoyuki, Muranaka, Atsuya, Hashizume, Daisuke, Uchiyama, Masanobu
Format: Article
Language:English
Subjects:
Benziphthalocyanine
Dimer
Near-infrared
Phthalocyanine
X-ray crystallography
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Summary:[Display omitted] •Methylene-bridged benziphthalocyanine dimer was synthesized at room temperature.•Single-crystal X-ray diffraction analysis revealed a V-shaped structure.•The dimer exhibited near-IR absorption and fluorescence. Methylene-bridged benziphthalocyanine dimer 2 was unexpectedly generated by the reaction of dihydroxybenziphthalocyanine 1 and formaldehyde in the presence of a catalytic amount of a base at room temperature. Single-crystal X-ray diffraction analysis of 2 revealed a V-shaped structure. Dimer 2 exhibited longer-wavelength absorption and fluorescence bands than monomer 1 in the near-IR region.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.04.089