Near-infrared absorbing pi-extended hexadeca substituted phthalocyanines

Pekbelgin Karaoğlu H. R., Atsay A., Nar I., McKee V., Koçak M., Hamuryudan E., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1197, ss.736-741, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1197
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.molstruc.2019.07.086
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.736-741
  • İstanbul Teknik Üniversitesi Adresli: Evet

Özet

Two new phthalonitriles 1 and 2, extended with biphenylethynyl and diphenylacetylenyl, were synthesized through a combination of Corey-Fuchs and palladium-catalyzed Sonogashira coupling reactions. The structures of 1 and 2 were revealed through single-crystal X-ray analysis. Cyclotetramerization of these phthalonitriles led to the corresponding 1,4,8,11,15,18,22,25-octabutoxy-2,3,9,10,16,17,23,24-octakis(biphenyl) and (diphenylacetylenyl) phthalocyanines. The longer substituent, namely diphenylacetylenyl, is slightly more effective than biphenyl in shifting the Q band to a longer wavelength. A cathodic shift in first oxidation potential indicated the destabilization of the HOMO energy levels that results from non-peripheral substitution and extended pi-conjugation. (C) 2019 Elsevier B.V. All rights reserved.