4960-25-2Relevant academic research and scientific papers
Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions
Li, Chao,Wan, Ke-Feng,Guo, Fu-Ya,Wu, Qian-Hui,Yuan, Mao-Lin,Li, Rui-Xiang,Fu, Hai-Yan,Zheng, Xue-Li,Chen, Hua
, p. 2158 - 2168 (2019/05/16)
Herein, an efficient and green method for the selective synthesis of tertiary amines has been developed that involves iridium-catalyzed alkylation of various primary amines with aromatic or aliphatic alcohols. Notably, the catalytic protocol enables this transformation in the absence of additional base and solvent. Furthermore, the alkylation of nitrobenzene with primary alcohol to tertiary amine has also been achieved by the same catalytic system. Deuterium-labeling experiments and a series of control experiments were conducted, and the results suggested that an intermolecular borrowing hydrogen pathway might exist in the alkylation process.
Posttreatment technique for SN2 alkylation of aromatics with alkyl halides: Aiming toward large-scale synthesis of building blocks for soft π-molecular materials
Okamoto, Ken,Lu, Fengniu,Nakanishi, Takashi
supporting information, p. 1258 - 1263 (2018/08/24)
Unreacted alkyl halide and byproduct olefin contaminants in products of SN2 alkylation reactions of aromatic compounds can be efficiently removed by sequential posttreatments with a base and a boron compound (sodium borohydride or 9- borabicyclo[3.3.1]nonane), followed by column chromatography on silica gel. These treatments permit large-scale purification of various alkylated aromatics, thereby assisting in the development of soft π-conjugated materials, such as monomers for semiconducting polymers or alkylated π-functional liquids.
Alkylation of Amines with Alcohols and Amines by a Single Catalyst under Mild Conditions
Zou, Qingzhu,Wang, Chao,Smith, Jen,Xue, Dong,Xiao, Jianliang
supporting information, p. 9656 - 9661 (2015/06/30)
An efficient catalytic system for the alkylation of amines with either alcohols or amines under mild conditions has been developed, using cyclometallated iridium complexes as catalysts. The method has broad substrate scope, allowing for the synthesis of a diverse range of secondary and tertiary amines with good to excellent yields. By controlling the ratio of substrates, both mono- and bis-alkylated amines can be obtained with high selectivity. In particular, methanol can be used as the alkylating reagent, affording N-methylated products selectively. A strong solvent effect is observed for the reaction.
Quadrupolar benzobisthiazole-cored arylamines as highly efficient two-photon absorbing fluorophores
Hrobrik, Peter,Hrobrikov, Veronika,Semak, Vladislav,Kask, Peter,Rakovsk, Erik,Polyzos, Ioannis,Fakis, Mihalis,Persephonis, Peter
supporting information, p. 6358 - 6361 (2015/02/19)
A computer-aided design of novel D-π-A-π-D styrylamines containing five isomeric benzobisthiazole moieties as the electron-accepting core has revealed the linear centrosymmetric benzo[1,2-d:4,5-d′]bisthiazole as the most promising building block for engin
Cruciform 9,10-distyryl-2,6-bis(p-dialkylamino-styryl)anthracene homologues exhibiting alkyl length-tunable piezochromic luminescence and heat-recovery temperature of ground states
Zheng,Zhang,Sun,Li,Liu,Xue,Yang
, p. 1913 - 1920 (2014/03/21)
A series of 2,6-bis(p-dialkylaminostyryl)-9,10-distyrylanthracene (FCn) cruciforms with N-alkyl chains of different lengths have been synthesized, and their aggregation-enhanced fluorescence and piezochromic luminescence (PFC) behaviours are investigated. These 9,10-distyrylanthracene-containing cruciforms exhibit relatively low fluorescence quantum yields (Φ) in THF solution (Φ ≈ 10%) and moderate aggregation-enhanced emission in aqueous media (Φ ≈ 25%), but strong and chain length-dependent solid-state fluorescence emission. Grinding and pressing experiments indicate that they are all effective PFC materials in terms of mechanical stress-induced spectral shifts (ΔλPFC = 23-54 nm), moreover, the longer alkyl-containing FCn shows a larger ΔλPFC. Powder X-ray diffraction and differential scanning calorimetry measurements reveal that the transformation between the crystalline and amorphous states upon external stimuli is responsible for the reversible PFC behaviour. It is found that increasing the N-alkyl length could effectively decrease the cold-crystallization temperature of the ground states to render the PFC states with a tunable heat-recovering temperature, and ground FC10 and FC12 solids can recover spontaneously to their original states at room temperature.
Synthesis, characterization, photophysics, and photosensitization studies of squaraine-bipyridinium diads
Liang, Kangning,Law, Kock-Yee,Whitten, David G.
, p. 540 - 546 (2007/10/03)
Two squaraine-bipyridinium diads designed to study electron transfer between the squaraine chromophore and the bipyridinium group have been synthesized. The two diads, denoted as C4Sq-By and C12Sq-By, consist of amphiphilic squaraines covalently linked to a bipyridinium group by a trimethylene chain. The squaraine chromophores in the diads do not form charge-transfer complexes with the bipyridinium group in the ground state. Both C4Sq-By and C12Sq-By show fluorescence yields about 100 times weaker than those of alkyl substituted squaraines, which is attributed to quenching by an intramolecular electron transfer from the excited squaraine chromophore to the bipyridinium; the intramolecular electron-transfer rate is estimated to be 4 × 1011 s-1. Assuming the short lifetime for the undetectable transient produced is due to very fast back electron transfer to the radical cation of squaraine from the reduced bipyridinium ion, the rate of the back intramolecular electron transfer is estimated as >3 ×1010 s-1. The two diads synthesized in this work have been used as photocurrent enhancers for the monolayers of DSSQ (4-(distearylamino)phenyl-4′-(dimethylamino)phenylsquaraine). C4Sq-By as a solution additive is 5 times more effective in sensitizing the cathodic photocurrent generation of the DSSQ monolayer-modified SnO2 electrode compared to methylviologen. Analogously, C12Sq-By is 3 times more effective in sensitizing the DSSQ monolayer-modified SnO2 electrode compared to 4-tetradecyl-4′-methylbipyridinium dichloride when it is incorporated upon spreading in the monolayer of DSSQ. The increase in cathodic photocurrent generation efficiency is postulated to result from fast electron transfer from the excited squaraine to the bipyridinium group in the diad. The fast electron transfer facilitates electron separation in the photogeneration step and consequently increases the quantum efficiency of the cathodic photocurrent generation process.
