The synthesis of novel, unsymmetrically substituted, chiral naphthalene and perylene diimides: Photophysical, electrochemical, chiroptical and intramolecular charge transfer properties

• Published in: Dyes and pigments Vol. 84; no. 1; pp. 1 - 13
• Main Authors: Asir, Suleyman, Demir, Ayhan S., Icil, Huriye
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 2010
• Subjects: Charge transfer; Chirality; Cyclic voltammetry; Exciplex; Unsymmetrical naphthalene diimides; Unsymmetrical perylene diimides; Exciplex; Cyclic voltammetry; Unsymmetrical perylene diimides; Unsymmetrical naphthalene diimides; Charge transfer; Chirality
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2009.04.014

A novel naphthalene monoimide and two unsymmetric chiral diimides (naphthalene and perylene) were synthesized; for comparison purposes, the perylene monoimide with the same substituent in the naphthalene monoimide was prepared. The naphthalene monoimide exhibited intramolecular charge transfer complexation in polar solvents. Excimer-like emissions were obtained in non-polar, polar protic and aprotic solvents in the cases of both the naphthalene monoimide and diimide. The specific optical rotation values of unsymmetrical chiral naphthalene and perylene diimides were −221.6 and −24, respectively at 20 °C. The Chiral naphthalene diimide showed prominent, negative Cotton effects centred at 362 and 382 nm in CH 3CN.