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

ZORLU Y., Kumru U., İŞCİ Ü., Divrik B., Jeanneau E., Albrieux F., ...More

CHEMICAL COMMUNICATIONS, vol.51, no.30, pp.6580-6583, 2015 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 51 Issue: 30
  • Publication Date: 2015
  • Doi Number: 10.1039/c5cc01085c
  • Page Numbers: pp.6580-6583


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.