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

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

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, respectivel...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2015-04, Vol.51 (30), p.6580-6583
Hauptverfasser: Zorlu, Yunus, Kumru, Ufuk, İşci, Ümit, Divrik, Burcin, Jeanneau, Erwann, Albrieux, Florian, Dede, Yavuz, Ahsen, Vefa, Dumoulin, Fabienne
Format: Artikel
Sprache:eng
Schlagworte:
Absorption
Assembly
Conjugation
Crystal structure
Derivatives
Distortion
Macrocyclic compounds
Wavelengths
X rays
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Beschreibung
Zusammenfassung: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc01085c