Abstract
Reaction between concentrated solutions of phenotiazine containing trialdehyde building block 4,4′,4″-(10-phenothiazine-3,7,10-triyl)tribenzaldehyde and (1R,2R)-cyclohexane-1,2-diamine results in the formation of a yellow transparent film. Exhaustive characterization of this material indicates that it is the result of the assembly of a linear polymer resulting from the linking of imine-based macrocycles. Phenotiazine units confer to this plastic the optical properties characteristic of photocatalytic materials. The transparency of the obtained material enabled the performance of solvent-free photocatalytic processes. This concept is illustrated by the oxidation of liquid organic sulfides, which can be performed in a recyclable manner. According to selective quenching experiments, such processes are the result of the energy transfer to oxygen molecule, generating singlet oxygen that is able to activate the sulfide molecules directly.
Highlights
An emerging trend in modern chemistry is the design of photocatalytic processes to achieve the assembly of a variety of compounds of increasing complexity [1,2,3,4,5]
In the quest for new polymeric structures that integrate the photocatalytic unit phenyl phenothiazine (PTH), we performed a variation of a reported synthesis that previously yielded a single molecule organic cage [42]
The PTH-containing material was prepared by the imine condensation between the trialdehyde PTH building unit 4,40,400 -(10-phenothiazine-3,7,10-triyl)tribenzaldehyde
Summary
An emerging trend in modern chemistry is the design of photocatalytic processes to achieve the assembly of a variety of compounds of increasing complexity [1,2,3,4,5]. Attending to the need for reducing the energy demands of photocatalytic processes, and in order to use solar light, replacing UV irradiation with visible-light is a current priority [6,7]. For this reason, the design of photocatalysts containing visible-light chromophores has blossomed in recent years. A major portion of processes mediated by visible light used compounds of metals such as Ir or Ru [8]. The scarcity, high cost and toxicity of these metals has pushed forward the research on organic photocatalysts. Phenyl phenothiazine (PTH) derivatives have been successfully used in dye-sensitized solar cells (DSSCs) [9,10,11], water splitting [12], hydrogen production [13,14,15,16,17], pollutant degradation [18] and organic synthesis [19,20,21,22]
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