Photochromism of tetrahydroindolizines. Part XIV: Synthesis of cis-fixed conjugated photochromic pyridazinopyrrolo[1,2-b]isoquinolines incorporating carbon-rich linkers

Abstract

New carbon-rich photochromic tetrahydroindolizines (THIs) bearing dihydroisoquinoline derivatives as heterocyclic bases (region B) have been synthesized via different chemical and photochemical pathways. Three alternative pathways for the synthesis of the target photochromic THI-based pyridazinopyrrolo[1,2-b]isoquinolines via in situ trapping with hydrazine hydrate have been established. In order to obtain high product yields, different Sonogashira-mediated coupling reactions have been optimized. Low temperature multichannel UV-vis and flash photolysis techniques were used to detect the photochromic and kinetic properties of the synthesized system. © 2014 Elsevier Ltd. All rights reserved.