50469-71-1

Upstream product

• 33816-51-2 5-bromo-2-methoxycyclohepta-2,4,6-trien-1-one 
• 105-56-6 ethyl 2-cyanoacetate 
• 101421-18-5 2,4-dibromo-cycloheptatrienone 
• 123-75-1 pyrrolidine 
• 110-89-4 piperidine 
• 110-91-8 morpholine 
• 38768-08-0 2-(tosyloxy)tropone 
• 3839-48-3 2-chlorotropone 
• 533-75-5 2-hydroxy-2,4,6-cycloheptatrien-1-one 
• 101495-29-8 2,4-dichloro-cycloheptatrienone 
• 36044-40-3 diethyl 2-chloroazulene-1,3-dicarboxylate 
• 3806-02-8 diethyl 2-aminoazulene-1,3-dicarboxylate 

Downstream Products

• 1157-45-5 diethyl 6-bromoazulene-1,3-dicarboxylate 
• 2013-05-0 diethyl 2-amino-6-styryl-1,3-azulenedicarboxylate 

Relevant academic research and scientific papers

Coordination Polymer Framework Based On-Chip Micro-Supercapacitors with AC Line-Filtering Performance

On-chip micro-supercapacitors (MSCs) are important Si-compatible power-source backups for miniaturized electronics. Despite their tremendous advantages, current on-chip MSCs require harsh processing conditions and typically perform like resistors when filtering ripples from alternating current (AC). Herein, we demonstrated a facile layer-by-layer method towards on-chip MSCs based on an azulene-bridged coordination polymer framework (PiCBA). Owing to the good carrier mobility (5×10?3 cm2 V?1 s?1) of PiCBA, the permanent dipole moment of azulene skeleton, and ultralow band gap of PiCBA, the fabricated MSCs delivered high specific capacitances of up to 34.1 F cm?3 at 50 mV s?1 and a high volumetric power density of 1323 W cm?3. Most importantly, such MCSs exhibited AC line-filtering performance (?73° at 120 Hz) with a short resistance–capacitance constant of circa 0.83 ms.

Synthesis of 2,6-diaminoazulenes by the snar reaction with cyclic amines

2-Amino-6-bromoazulene derivatives reacted with cyclic amines (pyrrolidine, piperidine and morpholine) under the sealed-tube conditions to afford the corresponding 2,6-diaminoazulenes in excellent yields.

Configuration-dependent optical properties and acid susceptibility of azulene compounds

We report the unique optical and protonation characteristics of azulene compounds with different molecular configurations and demonstrate their potential application as acid sensor materials. The unique characteristic of azulene compounds is its large dipole moment. Azulene derivatives with conjugation either along or orthogonal to the dipole direction of azulene were synthesized, and their electronic and optical properties were studied. Our results show that azulene with conjugation orthogonal to the dipole direction exhibits significant change in optical properties upon protonation due to strong intermolecular charge transfer. The low band gap absorption can reach up to mid-IR range, albeit at high acid doping concentration. On the other hand, conjugated azulenes along the dipole direction could be easily protonated even at very low acid concentration (ppm level), which is attributed to the formation of co-planar structures upon protonation and to their high proton affinity. Mechanisms behind the discrepancy between the two configurations are elucidated and further supported by computer simulation. The application of azulene chromophores as a chemical sensor with sensitivity at ppm level was also demonstrated in this work.

Modulating intramolecular electron and proton transfer kinetics for promoting carbon dioxide conversion

A novel pentagon-heptagon paired azulene group that possesses a large dipole moment is immobilized onto a porphyrin. The as-prepared azulene iron porphyrin exhibits a narrower bandgap and higher electrocatalytic CO2 reduction activity than the pristine iron porphyrin. The maximum CO faradaic efficiency reaches 99.9%, which is the state-of-the-art value among molecular catalysts. This journal is

Syntheses and properties of linear π-conjugated molecules composed of 1-azaazulene and azulene

Two compounds, 6-(1-azaazulen-2-yl)ethynylazulene (8) and 6-(2-azulenyl)ethynylazulene (10), were synthesized using the Sonogashira-Hagihara cross-coupling reaction followed by decarboxylation with concentrated phosphoric acid. Compounds 8 and 10 were cha

Azulene-Derived Fluorescent Probe for Bioimaging: Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy

Two-photon fluorescence microscopy has become an indispensable technique for cellular imaging. Whereas most two-photon fluorescent probes rely on well-known fluorophores, here we report a new fluorophore for bioimaging, namely azulene. A chemodosimeter, c

Synthesis of 2- and 6-thienylazulenes by palladium-catalyzed direct arylation of 2- and 6-haloazulenes with thiophene derivatives

Preparation of 2- and 6-thienylazulene derivatives was established by the palladium-catalyzed direct cross-coupling reaction of 2- and 6-haloazulenes with the corresponding thiophene derivatives in good yield. Several thienylazulene derivatives were also used in the reaction with 2-chloroazulene derivatives in the presence of the palladium-catalyst to afford the thiophene derivatives with two azulene functions in good yield.

The 2,6-diisocyanoazulene motif: Synthesis and efficient mono- and heterobimetallic complexation with controlled orientation of the azulenic dipole

Synthesis of the remarkably air- and thermally stable 2,6-diisocyano-1,3- diethoxycarbonylazulene linker from 2-amino-1,3-diethoxycarbonylazulene in 57% cumulative yield was developed. Incorporation of the ester "arms" in the design of this first diisocyanoazulene bridge permitted fully controlled stepwise installation and complexation of its isocyano junction groups. The -CC2Et arms in 2,6-diformamido-1,3-diethoxycarbonylazulene effectively suppress the rate of dehydration of its 2-NHCHO end relative to that of the 6-NHCHO end leading to practically exclusive formation of 6-isocyano-2-formamido-1,3-diethoxycarbonylazulene upon treatment of the above diformamide with an equimolar amount of POCl3. This crystallographically characterized 6-isocyano-2-formamidoazulene derivative was employed to access mono- and heterobimetallic complexes of the 2,6-diisocyanoazulene scaffold with controlled orientation of the azulenic dipole. A complete series of monometallic, homobimetallic, and isomeric heterobimetallic ([M] = M(CO)5, M = Cr and/or W) complexes of the 2,6-diisocyanoazulene motif was isolated and studied by a variety of techniques, including X-ray crystallography. The metal-to-bridge charge transfer in mono- and dinuclear adducts of 2,6-diisocyanoazulene, the assignment of which was corroborated by time-dependent density functional theory calculations, occurs at a dramatically lower energy as compared to the analogous systems featuring the 1,4-diisocyanobenzene scaffold. Moreover, the metal-to-diisocyanide charge transfer exhibits a substantially greater red shift upon binucleation of the mononuclear [M(CO)5] adducts of the nonbenzenoid 2,6- diisocyanoazulene linker versus the 1,4-diisocyanobenzene bridge.