Novel naphthalene diimides and a cyclophane thereof: synthesis, characterization, photophysical and electrochemical properties.
Three novel naphthalene diimides (1-3) and a cyclophane (4) containing two naphthalene diimide moieties were synthesized and characterized. In contrast to the absorption spectra, the emission spectra were strongly dependent on the solvent polarity. The excimer-like emission and low fluorescence rate constant suggest the formation of ground state complexes in DMF. All the compounds have low fluorescence quantum yields (0.001-0.012). They undergo reversible electron reduction and oxidation while deltaEp values depend strongly on solvent polarity. The LUMO energy values of 1 (3.76 eV), 2 (3.69 eV), and 3 (3.66 eV) vary with the substituent pattern. The structurally relatively rigid cyclophane 4 exhibits excellent thermal stability, a high glass transition temperature (tg, 102 degrees C) and a low LUMO energy value (3.59 eV). Compound 2 is insoluble in DMF at room temperature, but begins to dissolve at 37 degrees C and could therefore potentially serve as a sensor in temperature-sensing devices.
Ozser
Mustafa E
ME
Max-Planck-Institut für Strahlenchemie, D-45413 Mülheim an der Ruhr, Germany.
Uzun
Duygu
D
Elci
Idil
I
Icil
Huriye
H
Demuth
Martin
M
D004563:Electrochemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D006358:Hot Temperature; D007094:Imides; D009281:Naphthalenes; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry; D010777:Photochemistry; D013057:Spectrum Analysis
D004988:Ethers, Cyclic; D007094:Imides; D009281:Naphthalenes; D010618:Phenanthrolines; C542131:naphthalenediimide