Molecular structure and spectral properties of thionaphthalimides

Leonid D. Patsenker, Yevgeniya Ye Artyukhova

Research output: Contribution to journalArticlepeer-review

22 Scopus citations


The molecular structure and absorption spectra of monothio- and dithio-naphthalimides were compared to their naphthalimide analogues using AM1, PM3 and ZINDO/S semiempirical quantum chemical methods. The substitution of the 4R-naphthalimide oxygen atoms by sulphur atoms resulted in a red-shift of the absorption spectra by Δλmax60-65 and 100-140nm, respectively. The thionated naphthalimide derivatives do not show observable fluorescence due to intersystem crossing to the triplet nπ*-states localised at the C=S groups. The nπ*-absorption bands of monothioimides are located at 525-580 nm (ε = 60-80) and those for dithioimides at 535-560 nm (ε = 140-390) and 628-686 nm (ε = 34-68). None of these transitions are solvent sensitive. The nπ*-transitions of N-phenylthioimides have also a small contribution from nπ*-states due to a partial conjugation between C=S group and π-electronic system of the N-phenyl ring. As a result, the nπ* bands of aromatic substituted N-phenylthioimides are red-shifted as compared to those of the aliphatic N-methyl-thioimides.

Original languageEnglish
Pages (from-to)311-320
Number of pages10
JournalJournal of Molecular Structure
Issue number2
StatePublished - 29 Jul 2003
Externally publishedYes


  • Absorption spectra
  • Nπ*-Bands
  • Semiempirical calculations
  • Thio-naphthalimides


Dive into the research topics of 'Molecular structure and spectral properties of thionaphthalimides'. Together they form a unique fingerprint.

Cite this