A reversible molecular switches based on halogen substituted benzylidenehydantoins

Abstract

Molecular switches that can undertake reversible switching between two or more different states due to an external triggering stimulus are employed in the fabrication of various optoelectronic devices and smart materials and also found many applications in sensing, molecular self-assembly and photo-controlled biological systems. Photochromic organic molecules possessing bistable characteristics, represent attractive materials for the design of molecular switches owing to their considerable structural diversity, molecular conformations, electronic structures, and the possibility to reversibly alter from one state to another by external stimulations such as light irradiation. In this article, we explore the potential of halogen substituted benzylidenehydantoin-based molecules as novel light-sensitive materials and their solvatochromic behavior by recording the absorption spectra in the selected solvent set and evaluating effects of the specific and nonspecific solvent–solute interactions on the absorption maxima shifts using linear solvatation energy relationship, i.e. equations proposed by Kamlet-Taft and Katalan.. The preliminary results of this study will be promising starting point for design of novel photoactive materials with a broad spectrum of applications.

Molekulski prekidači koji se mogu mogu reverzibilno prevoditi iz jednog stabilnog stanja u drugo pod dejstvom nekog spoljašnjeg faktora, uveliko se primenjuju u proizvodnji različitih optičkih i elektronskih uređaja, pametnih materijala kao i raznovrsnih materijala sa biološkom primenom. Bistabilni fotohromni organski molekuli, predstavljaju akraktivne materijale za proizvodnju molekulskih prekidača zahvaljujući svojoj strukturnoj raznovrsnosti, molekulskim konformacijama, elektronskim karakteristikama i mogućnosti prevođenja iz jednog stabilnog stanja u drugo pod dejstvom svetlosti. U ovom radu, proučavana je mogućnost primene halogen supstituisanih benzilidenhidantoina u proizvodnji fotosenzitivnih materijala kao i njihova solvatohromna svojstva određivanjem odgovarajućih apsorpcionih maksimuma u odabranom setu rastvarača, a takođe su analizirani specifični i nespecifični efekti rastvarača na pomeranje apsorpcionih maksimuma primenom Kamlet-Taftove i Katalanove jednačine. Preliminarni rezultati ovog istraživanja predstavljaju dobru polaznu tačku u dizajniranju novih fotoaktivnih materijala sa širokim spektrom primene.