1431215-62-1

Basic information

• Product Name: (Z)-3-(4-methoxystyryl)-9-tert-butoxycarbonyl-9H-carbazole
• CAS NO: 1431215-62-1
• Molecular Weight: 399.489
• Mol File: 1431215-62-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-3-(4-methoxystyryl)-9-tert-butoxycarbonyl-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3-(4-methoxystyryl)-9-tert-butoxycarbonyl-9H-carbazole(1431215-62-1)
• EPA Substance Registry System: (Z)-3-(4-methoxystyryl)-9-tert-butoxycarbonyl-9H-carbazole(1431215-62-1)

Safety Data

• Hazardous Substances Data: 1431215-62-1(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 51761-07-0 9H-carbazole-3-carbaldehyde 
• 953797-80-3 3-formyl-9-tert-butoxycarbonyl-9H-carbazole 
• 1530-38-7 ((4-methoxyphenyl)methyl)triphenylphosphonium bromide 

Relevant articles and documents

Helicity as a steric force: Stabilization and helicity-dependent reversion of colored o-quinonoid intermediates of helical chromenes

Photolysis of regioisomeric helical chromenes 1 and 2 leads to colored reactive intermediates. While the latter generally decay quite rapidly, they are found to be longer lived in 1 and highly persistent in 2. The remarkable stability of the otherwise fleeting transient in 2 allowed isolation and structural characterization by X-ray crystallography. The structural analyses revealed that steric force inherent to the helical scaffold is the origin of stability as well as differentiation in the persistence of the intermediates of 1 and 2 (1Q and 2Q). The structure further shows that diphenylvinyl moiety in the TT isomer of 2Q gets splayed over the helical scaffold such that it is fraught with a huge steric strain to undergo required bond rotations to regenerate the precursor chromene. Otherwise, reversion of 2Q was found to occur at higher temperatures. Aazahelical chromenes 3 and 4 with varying magnitudes of helicity were designed in pursuit of o-quinonoid intermediates with graded activation barriers. Their photogenerated intermediates 3Q and 4Q were also isolated and structurally characterized. The activation barriers for thermal reversion of 2Q-4Q, as determined from Arrhenius and Eyring plots, are found to correlate nicely with the helical turn, which decisively determines the steric force. The exploitation of helicity is thus demonstrated to develop a novel set of photoresponsive helicenes 2-4 that lead to colored intermediates exhibiting graded stability. It is further shown that the photochromism of 2-4 in conjunction with response of 2Q-4Q to external stimuli (acid, heat, and visible radiation) permits development of molecular logic gates with INHIBIT function.