Bisphthalonitrile with a Disulfide-Based Linker and its Dimethylene Analogue: Comparative Structural Insights

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Alpugan S., Ekineker G., Ahsen V., Berber S., Onal E., DUMOULIN F.

CRYSTALS, vol.6, no.8, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 6 Issue: 8
  • Publication Date: 2016
  • Doi Number: 10.3390/cryst6080089
  • Journal Name: CRYSTALS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Acibadem Mehmet Ali Aydinlar University Affiliated: No

Abstract

Phthalonitriles are key precursors of phthalocyanines. Self-quenching dimeric phthalocyanines likely to be cleaved into monomeric species are of potential interest for tumour-site activated photosensitisers. Disulfide linkers can be specifically cleaved in tumoral tissue do to their reductive nature. Hence, a disulfide-linked phthalonitrile was designed to serve as further precursor of specifically tumour-activatable phthalocyanine-based photosensitising systems. Bisphthalonitrile with a disulfide-based linker and its dimethylene analogue were comparatively analyzed on a spectroscopic point of view as well as with DFT calculations. A thorough crystallographic analysis of the disulfide-linked derivative was conducted.