title: Novel anthracene materials for applications in lithography and reversible photoswitching by light and air.
abstract: Herein we demonstrate how the photoreaction between anthracenes and singlet oxygen ((1)O(2)) is employed for applications either as photoswitch or as photoresist. Thin films of the diaryl-alkyl anthracene 1 and the analogous oligomeric species 2 were irradiated under photomasks to generate pattern structures composed of 1/1-O(2) and 2/2-O(2). Kelvin probe force microscopy (KPFM) provided a powerful and nondestructive method to image the pattern information. The following studies based on AFM, KPFM and contact angle measurements unfold that the two species 1 and 2 underwent different progressions after the imaging step. Degrading is observed for the monomeric compound 1 and the pattern eventually becomes recognizable in topography. In the oxidized state (1-O(2)) the monomeric species remains physically stable. In consequence, the unreacted portion is removable and the remaining oxygenated form 1-O(2) is sufficiently stable to protect an underlying substrate (e.g., silver) from etching. Thus, the system 1/1-O(2) operates as photoresist. On the other hand, both states of the oligomer 2 remain stable. The film is stable up to temperatures >120 degrees C required to erase the pattern within acceptable time by cycloreversion. Anthracene 2 therefore acts as erasable and rewritable photochromic switch. The different behavior between 1 and 2 is explained by phase transitions which cause crystallization and finally ablation. Such transitions affect only the monomeric system 1/1-O(2) and not the oligomeric system 2/2-O(2). In conclusion, we designed two very similar materials based on diarylanthracenes, which can act either as a photoresist or as a rewritable photochromic switch.
authors.affiliation: Department of Chemistry, University of Potsdam, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam/Golm, Germany.
authors.forename: Werner
authors.initials: W
authors.lastname: Fudickar
authors.forename: Torsten
authors.initials: T
authors.lastname: Linker