1,4,8,11,15,18,22,25-Alkylsulfanyl phthalocyanines: effect of macrocycle distortion on spectroscopic and packing properties

Chemical Communications : Chem Comm
Yunus ZorluFabienne Dumoulin

Abstract

The effect of phthalocyanine macrocycle distortion on its spectroscopic and packing properties is studied, by comparing two phthalocyanines octa-non-peripherally substituted by alkanethiols of different bulkiness (n-hexyl and tert-butyl). Their X-ray structures evidence their core shape, respectively planar and strongly distorted, inducing a 55 nm shift of their maximum absorption wavelength. Comparison of frontier orbital energies revealed that this distortion decreases the conjugation potency of the benzo rings to the central pyrrolic rings. Also the tert-butyl derivative presents a MOF-like porous crystalline assembly with 22.2% void.

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Citations

Aug 24, 2016·The Journal of Physical Chemistry. a·Christopher FarleyCharles Michael Drain
May 8, 2019·Chemical Communications : Chem Comm·Declan McKearneyDaniel B Leznoff
Jul 28, 2018·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Anzhela Galstyan, Ulrich Dobrindt

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