1404291-53-7

Upstream product

• 298212-99-4 2-(4-iodophenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1404291-52-6 2-(4′-iodophenyl)-7,8-dibromo-7,8,1,8a-tetrahydroazulene-1,1-dicarbonitrile 
• 1448895-80-4 C₁₈H₁₀BrIN₂ 

Downstream Products

• 1404291-54-8 2-[4'-methylthio(1,1'-biphenyl)-4-yl]-7-bromo-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1448895-80-4 C₁₈H₁₀BrIN₂ 
• 1404291-50-4 2-[4′-methylthio(1,1′-biphenyl)-4-yl]-7-[4-(methylthio)phenyl]-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1514925-29-1 2-([1,1-biphenyl]-4-yl)-7-phenyl-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1430198-77-8 7-(trimethylstannyl)-2-[4-(trimethylstannyl)phenyl]-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1430198-82-5 7-(trimethylstannyl)-2-[4-(trimethylstannyl)phenyl]azulene-1-carbonitrile 
• 1430198-70-1 2-(4'-(tert-butylthio)-[1,1'-biphenyl]-4-yl)-7-[4-(tertbutylthio)phenyl]-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 1430198-73-4 S-[4-[2-(4'-(acetylthio)[1,1'-biphenyl]-4-yl)-3,3-dicyano-3,3a-dihydroazulen-5-yl]phenyl]ethanethioate 
• 1430198-85-8 C₃₄H₂₄N₂O₂S₂ 

Relevant academic research and scientific papers

Photoswitching of Dihydroazulene Derivatives in Liquid-Crystalline Host Systems

Photoswitches and dyes in the liquid-crystalline nematic phase have the potential for use in a wide range of applications. A large order parameter is desirable to maximize the change in properties induced by an external stimulus. A set of photochromic and nonphotochromic dyes were investigated for these applications. It was found that a bent-shaped 7-substituted dihydroazulene (DHA) photoswitch exhibited liquid-crystalline properties. Further investigation demonstrated that this material actually followed two distinct reaction pathways on heating, to a deactivated form by a 1,5-sigmatropic shift and to a linear 6-substituted DHA. In addition, elimination of hydrogen cyanide from the photoactive DHA gave both bent and linear azulene dyes. In a nematic host that has no absorbance around 350 nm, it was found that only the linear DHA derivative has nematic properties; however, both 6- and 7-substituted DHAs were found to have large order parameters. In the nematic host, ring opening of either DHA to the corresponding vinylheptafulvene resulted in a decrease in dichroic order parameter and an unusually fast back-reaction to a mixture of both DHAs. Likewise, only the linear azulene derivative showed mesomorphic properties. In the same nematic host, large order parameters were also observed for these dyes.

Palladium-mediated strategies for functionalizing the dihydroazulene photoswitch: Paving the way for its exploitation in molecular electronics

The dihydroazulene (DHA)/vinylheptafulvene (VHF) photo/thermoswitch has attracted interest as a molecular switch for advanced materials and molecular electronics. We report here two synthetic approaches using palladium catalysis for synthesizing dihydroazulene (DHA) photoswitches with thioacetate anchoring groups intended for molecular electronics applications. The first methodology involves a Suzuki coupling using tert-butyl thioether protecting groups. Conversion to the thioacetate using boron tribromide/acetyl chloride results in the formation of the product as a mixture of regioisomers mediated by a ring-opening reaction. The second approach circumvents isomerization by the synthesis of stannanes as intermediates and their use in a Stille coupling. Although fully unsaturated azulenes are formed as byproducts during the synthesis of the DHA stannanes, this approach allowed the regioselective incorporation of the thioacetate anchoring group in either one of the two ends (positions 2 or 7) or at both.

Dihydroazulene photoswitch operating in sequential tunneling regime: Synthesis and single-molecule junction studies

Molecular switches play a central role for the development of molecular electronics. In this work it is demonstrated that the reproducibility and robustness of a single-molecule dihydroazulene (DHA)/vinylheptafulvene (VHF) switch can be remarkably enhance