Diaryltrisphaeridine Derivatives: Synthesis, Experimental Electrochemical and Photophysical Properties, and Theoretical Studies

Abstract

A series of diaryltrisphaeridines have been synthesized by iodination of trisphaeridine and subsequent Suzuki coupling reactions. The photophysical and electrochemical properties of these compounds have been investigated and it has been found that they are dependent on the aryl substituents. In particular, the presence of dimethylamino groups induces a bright‐green emission, thus making this compound a promising candidate for fluorescence devices and molecular sensors. Moreover, the green emission disappears on addition of HCl and this material can therefore also be used as a sensor for protons. The results have been rationalized by DFT and TD‐DFT theoretical studies.

Iodination of Isoquinoline by Trifluoromethanesulfonic Acid

“…In the same year, Denny group described the synthesis and structure‐activity relationships for related heterocyclic derivatives of Tetracyclic Phenazines which iodoisoquinolines was key intermediate during the synthesis process [11] (Scheme 1b). In 2012, Rodríguez group has reported metal‐free electrophilic iodination of trisphaeridine with I(pyridine) 2 BF 4 which as substrate in Suzuki coupling reaction [12] (Scheme 1c). In 2013, Mulder founded an economical and safe method to synthesis methyl 6‐chloro‐5‐(trifluoromethyl)nicotinate.…”