14658-95-8Relevant academic research and scientific papers
Synthesis and crystal structures of N,N-diarylacetamides bearing two azulene rings
Ito, Ai,Watanabe, Mayuko,Ishii, Ayako,Yamasaki, Ryu,Okamoto, Iwao
supporting information, (2021/11/22)
N,N-Diarylacetamides bearing two azulene rings on the amide nitrogen were synthesized and their crystal structures were determined. The dihedral angle between the amide plane and the aryl ring located on the same side as the amide oxygen atom is influenced by the position of linkage of the aromatic ring to the nitrogen atom, and a 2-azulenyl group located on the same side as amide oxygen atom tends to be coplanar with the amide plane. This feature may be useful in the design of molecular devices and supramolecules.
Configuration-dependent optical properties and acid susceptibility of azulene compounds
Tang, Tao,Lin, Tingting,Erden, Fuat,Wang, Fu Ke,He, Chaobin
, p. 5153 - 5160 (2018/05/28)
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.
Synthesis and structural characterization of diazulenylborinic acid
Murafuji, Toshihiro,Shintaku, Kohhei,Nagao, Kouhei,Mikata, Yuji,Ishiguro, Katsuya,Kamijo, Shin
, p. 676 - 690 (2017/05/02)
Diazulenylborinic acid 1 was synthesized by the reaction of 1,3-dibromoazulen-2-yllithium (2) with 1,3-dibromoazulen-2-ylboronic acid ethylene glycol ester (7d). The X-Ray crystallographic study of 1 revealed that it forms a dimeric structure through intermolecular hydrogen bonding between the hydroxyl groups. To obtain the tetracoordinate borinate derivative from 1, the attempted esterification of 1 with N,N-dimethylethanolamine did not give corresponding borinate 8 but resulted in the unexpected protodeboronation to give parent 1,3-dibromoazulene (4). The 13C and 11B NMR studies of 1 in the presence of Et3N revealed the change in the φ-polarization of the azulenyl group accompanied by the change in the geometry of the boron to a tetracoordinate structure.
Antiretroviral (HIV-1) activity of azulene derivatives
Peet, Julia,Selyutina, Anastasia,Bredihhin, Aleksei
, p. 1653 - 1657 (2016/04/05)
The antiretroviral activity of azulene derivatives was detected for the first time. A series of eighteen diversely substituted azulenes was synthesized and tested in vitro using HIV-1 based virus-like particles (VLPs) and infectious HIV-1 virus in U2OS and TZM-bl cell lines. Among the compounds tested, the 2-hydroxyazulenes demonstrated the most significant activity by inhibiting HIV-1 replication with IC50 of 2-10 and 8-20 μM for the VLPs and the infectious virus, respectively. These results indicate that azulene derivatives may be potentially useful candidates for the development of antiretroviral agents.
A convenient synthesis of functionalized azulenes via negishi cross-coupling
Dubovik, Julia,Bredihhin, Aleksei
, p. 538 - 548 (2015/02/19)
A mild and effective method for the synthesis of functionalized azulenes is described. Negishi cross-coupling of bromoazulenes with functionalized aromatic, heterocyclic, benzylic, and alkylic organozinc reagents affords substituted azulenes in good yields. Functional groups, including ethoxycarbonyl, cyano, methoxy, fluoro, chloro, and bromo are well tolerated. Additionally, a one-pot procedure for introducing two different substituents into positions 1 and 3 of azulene through cross-coupling reaction is described for the first time.
Hole-Transporting Materials with a Two-Dimensionally Expanded π-System around an Azulene Core for Efficient Perovskite Solar Cells
Nishimura, Hidetaka,Ishida, Naoki,Shimazaki, Ai,Wakamiya, Atsushi,Saeki, Akinori,Scott, Lawrence T.,Murata, Yasujiro
supporting information, p. 15656 - 15659 (2016/01/09)
Two-dimensionally expanded π-systems, consisting of partially oxygen-bridged triarylamine skeletons that are connected to an azulene (1-3) or biphenyl core (4), were synthesized and characterized. When tetra-substituted azulene 1 was used as a hole-transporting material (HTM) in perovskite solar cells, the observed performance (power conversion efficiency = 16.5%) was found to be superior to that of the current HTM standard Spiro-OMeTAD. A comparison of the hole mobility, the ability to control the HOMO and LUMO levels, and the hole-collection efficiency at the perovskite/HTM interface in 1 with reference compounds (2-4 and Spiro-OMeTAD) led to the elucidation of key factors required for HTMs to act efficiently in perovskite solar cells.
1-Phenylselanylazulenes: Synthesis and selenium atom oxidation
Razus, Alexandru C.,Birzan, Liviu,Hanganu, Anamaria,Cristea, Mihaela,Ungureanu, Eleonora-Mihaela,Soare, Maria-Laura,Buica, George-Octavian
, p. 1999 - 2009 (2015/02/19)
The phenylselanylation of azulene with PhSeCl or PhSeBr was reported. Clean electrophilic substitution of azulene in positions 1 and/or 3 occurred with the first reagent whereas with PhSeBr a complex mixture of products was generated suggesting a radicali
Azulene-containing organic chromophores with tunable near-IR absorption in the range of 0.6 to 1.7 μm
Wang, Fuke,Lin, Ting Ting,He, Chaobin,Chi, Hong,Tang, Tao,Lai, Yee-Hing
scheme or table, p. 10448 - 10451 (2012/09/07)
Near-infrared (NIR) absorption in the range of 0.75-2.5 μm is in great demand for a variety of applications but currently the majority of commercial NIR devices are based on inorganic materials due to the limited number of organic materials that are active in this range. Here we present the preparation and optical studies of a new series of stable azulene-containing NIR chromophores whose absorption can be tuned in the range of 0.6-1.7 μm. DFT calculation revealed that the protonation-induced low excitation gap was attributable to the substantial intramolecular charge transfer. The Royal Society of Chemistry 2012.
1,3-Di(2-pyrrolyl)azulene: An efficient luminescent probe for fluoride
Salman, Husein,Abraham, Yael,Tal, Shay,Meltzman, Shai,Kapon, Moshe,Tessler, Nir,Speiser, Shammai,Eichen, Yoav
, p. 2207 - 2212 (2007/10/03)
Photo-induced Energy Transfer (PET) based chemosensing is a very elegant way for reporting the presence of an analyte in solution. This method was successfully applied to the detection of many canonic species in solutions and already appears in interesting commercial applications, in this paper we report on the preparation and host-guest chemistry of 1,3-di(2-pyrrolyl)azulene (5), a new azulene-based selective PET-like chemosensor that turns fluorescent upon binding the fluoride anion. Willey-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
The first fully characterized 1,3-polyazulene: High electrical conductivity resulting from cation radicals and polycations generated upon protonation
Wang, Fuke,Lai, Yee-Hing,Kocherginsky,Kosteski, Yu.Yu.
, p. 995 - 998 (2007/10/03)
Figure presented 1,3-Polyazulene prepared by the chemical polymerization of 1,3-dibromoazulene with Ni(COD)2 was aptly characterized by spectroscopic analysis. The azulene units remain intact in the isolated polymer. Protonation of 1,3-polyazulene by trifluoroacetic acid was found to exhibit high conductivity and paramagnetic properties via the formation of cation radicals and di- and polycations.
