Key Electronic,Linear and Nonlinear Optical Properties of Designed Disubstituted Quinoline with Carbazole Compounds

Organic materials development, especially in terms of nonlinear optical (NLO) performance, has become progressively more significant owing to their rising and promising applications in potential photonic devices. Organic moieties such as carbazole and quinoline play a vital role in charge transfer applications in optoelectronics. This study reports and characterizes the donor–acceptor–donor–π–acceptor (D–A–D–π–A) configured novel designed compounds, namely, Q3D1–Q3D3, Q4D1–Q1D2, and Q5D1. We further analyze the structure–property relationship between the quinoline–carbazole compounds for which density functional theory (DFT) and time-dependent DFT (TDDFT) calculations were performed at the B3LYP/6-311G(d,p) level to obtain the optimized geometries, natural bonding orbital (NBO), NLO analysis, electronic properties, and absorption spectra of all mentioned compounds. The computed values of λ_max, 364, 360, and 361 nm for Q3, Q4, and Q5 show good agreement of their experimental values: 349, 347, and 323 nm, respectively. The designed compounds (Q3D1–Q5D1) exhibited a smaller energy gap with a maximum redshift than the reference molecules (Q3–Q5), which govern their promising NLO behavior. The NBO evaluation revealed that the extended hyperconjugation stabilizes these systems and caused a promising NLO response. The dipole polarizabilities and hyperpolarizability (β) values of Q3D1–Q3D3, Q4D1-Q1D2, and Q5D1 exceed those of the reference Q3, Q4, and Q5 molecules. These data suggest that the NLO active compounds, Q3D1–Q3D3, Q4D1–Q1D2, and Q5D1, may find their place in future hi-tech optical devices.     

A Facile Synthesis of Benzo[h]quinolines via Silica‐TsOH‐P2O5 Promoted Condensation of 1‐Naphthylamines with 1,3‐Diketones under Solvent Free Conditions

A facile synthesis of benzo[h ]quinolines has been developed via improved Combes reaction. A combination of silica gel, p ‐toluenesulfonic acid and phosphorus pentoxide was utilized to promote the condensation of 1‐naphthylamines with 1,3‐diketones under solvent free conditions. In this case, silica gel was used as reaction media, p ‐toluenesulfonic acid and phosphorus pentoxide were acted as catalyst and dehydrating agent, respectively.     

Reaching for two new stable ambiphilic quinoline‐derived N‐heterocyclic carbenes at DFT level

A detailed investigation on the thermodynamic and kinetic stability of four carbenic tautomers of quinoline 1 , including quinoline‐2‐ylidene 2 , quinoline‐3‐ylidene 3 , quinoline‐4‐ylidene 4 , and 3,4‐dihydroquinoline‐4‐ylidene 5 , reveals that singlet planar six‐membered ring N‐heterocyclic carbenes (NHCs) 2 and 4 have less stability than Arduengo type NHC but seems to have enough conceivably for reaching at B3LYP/aug‐cc‐pVTZ//B3LYP/6–31+G* and B3LYP/6–311++G**//B3LYP/6–31+G* levels. All these six‐membered NHCs are extremely ambiphilic with the more nucleophilic and electrophilic characters compared to the Arduengo type one. The aromaticity of singlet 2 and 4 is a significant contributor to their stability which is confirmed through their Nucleus‐independent chemical shift(1)_zz values. Finally, among 2–5 , the normal NHC 2 is thermodynamically preferred but the remote NHC 4 is kinetically proffered over the other isomeric carbenes. The effects of different N‐ or C‐substituted NHCs of 2 are studied using appropriate isodesmic reactions. The trimethylsilyl substituent exhibits slightly larger carbene stabilization in quinoline‐derived NHCs than the pyridine analogue. © 2014 Wiley Periodicals, Inc.     

Synthesis of Novel 1,2,4‐oxadiazoline Derivatives Containing Quinoline Moiety by 1,3‐Dipolar Cycloaddition

A series of novel 1,2,4‐oxadiazoline derivatives containing 2‐(1,2,4‐triazol‐1‐yl)quinoline were synthesized by the reaction of imines with benzohydroximinoyl chlorides in the presence of Et₃N via 1,3‐diplolar cycloaddition reaction. The structures of the target compounds were confirmed by IR, ¹H NMR, MS, elemental, and X‐ray crystallographic analysis.     

PEG-assisted one-pot three-component synthesis of 1,3-oxazino quinoline and chromeno 1,3-oxazin derivatives under catalyst free condition

Abstract

A straightforward and greener PEG-assisted protocol has been disclosed for the cascade synthesis of [1,3]Oxazino quinoline, and chromeno[1,3]oxazin derivatives via three component reaction of multifarious aromatic amines with formaldehyde and 4-hydroxyquinoline-2(1H)-one or 4-methylumbelliferone by using very convenient reaction conditions. This methodology represents a sustainable approach for rapid access to a library of diversity oriented highly pure [1,3]oxazino scaffolds with broad substrate scope.     

Microwave‐assisted Friedländer Synthesis of Polysubstituted Quinolines Based on Poly(ethylene glycol) Bound Acetoacetate

Polysubstituted quinolines were efficiently prepared on the soluble polyethylene glycol (PEG) by microwave irradiation Friedländer condensation of PEG bound acetoacetate with 2‐aminoarylketones promoted by catalytic amount of polyphosphoric acid, and subsequently cleavage from the PEG with MeONa in MeOH. The polymer‐supported synthesis provided the target compounds in excellent yield and purity with a facile work‐up procedure.     

NiWS/γ-Al2O3催化剂上吲哚加氢脱氮反应:H2S和喹啉的影响

在连续固定床微反装置上考察了吲哚（IND）和1,2-二氢吲哚（HIN）在NiWS/γ-Al₂O₃催化剂上加氢脱氮（HDN）的反应以及 H₂S和喹啉（Q）对其加氢脱氮反应的影响。结果表明,碱性含氮化合物HIN较吲哚对其自身的加氢脱氮反应抑制作用更为明显。H₂S能够促进HIN的C（sp³）－N断裂,但抑制了邻乙基苯胺（OEA）的 C（sp²）－N断裂;同时吲哚加氢反应途径也受到了抑制。喹啉的添加严重降低了吲哚加氢脱氮反应的转化率和脱氮率;喹啉对吲哚加氢反应和C－N键断裂反应均产生明显的抑制作用。喹啉的抑制作用主要源于喹啉及其中间产物1,2,3,4-四氢喹啉（THQ1）和5,6,7,8 -四氢喹啉（THQ5）与吲哚及其中间产物的竞争吸附。     

2-(1-Aryliminoethylidene)quinolylnickel(II) dibromides: Synthesis, characterization and ethylene dimerization capability

A series of 2-(1-aryliminoethylidene)quinoline derivatives (L1-L9) and the nickel(II) dibromides (C1-C9) thereof, were synthesized and characterized. The molecular structures of C2 (R¹ = Et, R² = H, R = Me) and C9 (R¹ = ⁱPr, R² = H, R = ⁱPr) were confirmed as being distorted tetrahedral at nickel by single crystal X-ray diffraction. On treatment with diethylaluminium chloride (Et₂AlCl) or ethylaluminum sesquichloride (EASC), these nickel pre-catalysts exhibited high activity for selective ethylene dimerization (0.89-3.29 × 10⁶ g mol⁻¹(Ni) h⁻¹) at 20 °C under 10 atm of ethylene. The influence of the reaction parameters on the catalytic behaviour was investigated for these nickel systems, including variation of Al/Ni molar ratio and reaction temperature.     

1-(2-噻唑)-3-(8-(5-对磺酸基苯基偶氮)喹啉)-三氮烯的合成及其与铜(Ⅱ)的显色反应

合成了新试剂1-(2-噻唑)-3-(8-(5-对磺酸基苯基偶氮)喹啉-三氮烯(TCPQT),并研究了其与Cu2+的显色反应。结果表明:在pH 7.5的磷酸盐缓冲溶液中,TCPQT与Cu2+形成摩尔比为1:1的紫红色络合物,该络合物在606.5nm处有一最大吸收峰,其表观摩尔吸光系数为3.36×105L.mol-1.cm-1,Cu2+的质量浓度在0～0.4μg/mL范围内符合比尔定律,相关系数r=0.9993。方法已用于测定食品中的微量铜。     

邻溴苯胺/丙烯醛Schiff碱分子内Heck反应——合成喹啉的新方法

探讨了一种以邻溴苯胺和丙烯醛为原料合成喹啉的新方法,对反应条件进行了优化,并利用质谱和红外光谱分析确认了合成产物的结构.结果表明,以邻溴苯胺和丙烯醛为原料,经2步反应可得到喹啉:首先,邻溴苯胺和丙烯醛反应生成Schiff碱;随后,Schiff碱在催化剂和N2保护下经分子内Heck反应形成目标产物(总产率为45.1%).该合成方法具有操作简单、易于控制、催化剂可重复使用等优点.