Bis-spiropyrans containing an arylazo group based on indolo[4,5-e]indole

Author: Goga Khubashvili
Keywords: Iondoloindole, spiropyran, photochrome
Annotation:

Spiropyrans are the most important class of organic photochromes, which have received much attention from researchers in recent years. The photochromic properties of spiropyrans are significantly affected by various substituted groups in the hetarine part of the chromium fragment of the molecule. The purpose of this bachelor's work was the synthesis of a new hybrid bis-spiropyran, the molecule of which will combine the properties of two chromophore groups, spiropyran and azobenzene. It was interesting to study their mutual influence on the structure and properties of the molecule. The previously synthesized bis-analogue of Fischer's base hexamethyldimethylenindolino[4,5-e]indoline was chosen as the object of the study. By its condensation with azo-conjugated salicylic aldehydes, two new bisspiropyrans were synthesized: bis(6-azophenyl-2H-chromene-2-spiro) -1,1,3,8,10,10-hexamethyleneindolenino[4,5-e]indolenine and bis(6-azophenyl-8-methoxy-2H-chromen-2-spiro)-1,1,3,8, 10,10-hexamethylindolnino[4,5-e]-indolenine. In the electronic spectra of their alcohol solutions, absorption maxima are found at 233 (0.664), 337 (0.723) and 589 (0.056), while in the alcohol solution in the region of 586 (0.454) nm, and for methoxy-azo products, respectively, 383 (4.395) , 427(1.607), 593(1.156), (0.610), (0.118). In both cases, the absorption maximum in the long-wavelength region corresponds to the unilaterally open betaine form of bis-spiropyran. When studying the proton magnetic resonance spectrum, it is assumed that the obtained bisspiropyran molecule can exist in the form of an asymmetric unilaterally open form (its solutions are colored). They do not exhibit photochromic properties.

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Bis-spiropyrans containing an arylazo group based on indolo[4,5-e]indole [en]
არილაზო ჯგუფის შემცველი ბის-სპიროპირანები ინდოლო[4,5-e]ინდოლის საფუძველზე [ka]