216760-89-3

Upstream product

• 109-64-8 1,3-dibromo-propane 
• 2050-16-0 4,4'-dihydroxyazobenzene 
• 123-30-8 4-amino-phenol 

Downstream Products

• 141484-77-7 C₄₄H₃₆N₄O₄ 

Relevant academic research and scientific papers

New heterocyclic tetrathiafulvalene compounds with an azobenzene moiety: Photomodulation of the electron-donating ability of the tetrathiafulvalene moiety

(Chemical Equation Presented) New heterocyclic TTF compounds 1a-c and 2 with an azobenzene moiety were described. The oxidation potential of 1a could be reversibly modulated by alternating UV and visible light irradiation. As a result, a molecular switch

Rational design of a photoswitchable DNA glue enabling high regulatory function and supramolecular chirality transfer

Short, complementary DNA single strands with mismatched base pairs cannot undergo spontaneous formation of duplex DNA (dsDNA). Mismatch binding ligands (MBLs) can compensate this effect, inducing the formation of the double helix and thereby acting as a molecular glue. Here, we present the rational design of photoswitchable MBLs that allow for reversible dsDNA assembly by light. Careful choice of the azobenzene core structure results in excellent band separation of theEandZisomers of the involved chromophores. This effect allows for efficient use of light as an external control element for duplex DNA formation and for an in-depth study of the DNA-ligand interaction by UV-Vis, SPR, and CD spectroscopy, revealing a tight mutual interaction and complementarity between the photoswitchable ligand and the mismatched DNA. We also show that the configuration of the switch reversibly dictates the conformation of the DNA strands, while the dsDNA serves as a chiral clamp and translates its chiral information onto the ligand inducing a preference in helical chirality of theZisomer of the MBLs.

New photochromic azoderivatives with potent acetylcholinesterase inhibition

The design of photochromic cholinesterase inhibitors is a challenge of the photopharmacological approach towards the remote control of acetylcholinesterase (AChE) enzyme and its potential application in Alzheimer's disease therapy. In this work, a series of azoderivatives were designed, synthesized and evaluated as AChE inhibitors. The optimized microwave-assisted synthesis (two steps) showed excellent yields with a total reaction time no longer than 40 min. The results showed that all the synthesized compounds exhibited high AChE inhibitory activity at the micromolar range (IC50, 0.65–8.52 μM). Moreover, compound 19, with double four-hydrocarbon chain connected to piperidine, showed a powerful in vitro enzymatic response for its Z isomer (IC50: 0.43 μM) determined by Ellman's assay. Also, 19 showed a stable photostationary state monitored by UV/Vis absorption spectroscopy and 1H NMR spectra. These results indicate that 19 can act as an efficient photo-responsible probe to remote control AChE activity. Molecular modelling analysis of 19 Z revealed its affinity by the peripheral anionic site of AChE, providing understanding of its higher inhibition power. This study contributes to the development of new promising agents for photopharmacological treatment of Alzheimer's disease.

Effect of Structure of Photoresponsive Molecules on Photochemical Phase Transition of Liquid Crystals I. Synthesis and Thermotropic Properties of Photochromic Azobenzene Derivatives

Seventeen azobenzene derivatives were synthesized and their thermotropic properties were examined.They are classified into three groups.In the first group, 4-cyanobiphenyl moieties are attached to both sides of azobenzene through various alkyl spacers: AB(nCB)2 where n = 3, 4, 5 and 6.In the second group, the 4-cyanobiphenyl moiety is attached to one side of the azobenzene, while the substituent of the other side was kept as OCH3:1ABnCB, where n = 3, 4, 5, 6 and 8.The third group is the azobenzene derivatives which possess alkoxy substituents at both para positions of azobenzene (nABm) or at various positions of the azobenzene phenyl rings (k,1ABn,m).The introduction of the 4-cyanobiphenyl group at the end(s) of the molecules is based on the attempt of highly efficient photochromic molecules to induce photochemical phase transition of liquid crystals by providing the photochromic trigger molecules with high affinity to the host liquid crystal.Both 1ABnCB and AB(nCB)2 exhibited the liquid crystalline phases, whereas among nABm and k,1ABn,m, only 1AB8 and 8AB8 showed the liquid crystalline phase.The 1ABnCB series exhibited a distinct odd-even variation in phase transition temperatures as well as enthalpy and entropy changes with the length of the flexible spacers, while the AB(nCB)2 series did not show clear odd-even variation except for the liquid crystal to isotropic phase transition temperatures.