title: Novel naphthalene diimides and a cyclophane thereof: synthesis, characterization, photophysical and electrochemical properties.
abstract: 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.
authors.affiliation: Max-Planck-Institut für Strahlenchemie, D-45413 Mülheim an der Ruhr, Germany.
authors.forename: Mustafa E
authors.initials: ME
authors.lastname: Ozser
authors.forename: Duygu
authors.initials: D
authors.lastname: Uzun
authors.forename: Idil
authors.initials: I
authors.lastname: Elci
authors.forename: Huriye
authors.initials: H
authors.lastname: Icil
authors.forename: Martin
authors.initials: M
authors.lastname: Demuth
mesh_terms: 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
chemical_list: D004988:Ethers, Cyclic; D007094:Imides; D009281:Naphthalenes; D010618:Phenanthrolines; C542131:naphthalenediimide