Fluorescent macromolecular perylene diimides containing pyrene or indole units in bay positions

DİNÇALP H., Kizilok Ş., Içli S.

Dyes and Pigments, cilt.86, sa.1, ss.32-41, 2010 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 86 Sayı: 1
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1016/j.dyepig.2009.11.005
  • Dergi Adı: Dyes and Pigments
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.32-41
  • Anahtar Kelimeler: Perylene diimide, Pyrene, Solvatochromism, Charge transfer, HOMO-LUMO energy levels, DSSC
  • Manisa Celal Bayar Üniversitesi Adresli: Evet

Özet

Novel, symmetric and unsymmetric perylene diimide dyes with pyrene or indole units in the bay positions of the perylene ring were synthesized and characterized using FT-IR, 1H and 13C NMR, MS, UV-Vis spectra and cyclic voltammetry. The λmax in different solvents were in the range 526-585 nm and emission wavelengths of the dyes exhibited positive solvatochromism with increasing solvent polarity. Long wavelength emissions >750 nm of dyes with pyrene units displayed charge-separated state of perylene-pyrene system. Dyes with pyrene or indole units showed greater photostability in toluene than dyes which did not contain these bulky substituents. Incorporating electron-donating indole substituents lowered the band gap energies and, therefore, the HOMO energy levels were increased. The energy density and shape of the molecular orbitals were calculated theoretically. © 2009 Elsevier Ltd. All rights reserved.