Synthesis of new conjugated copolymers containing 4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b′]dithiophene/5,7-bis(3,4-diethylthien-2-yl)-2,3-diphenylthieno[3,4-b]pyrazine and 4,8-bis(dodecyloxy)benzo[1,2-b:4,5-b′]dithiophene/4,6-di(3,4-diethylthien-2-yl)-thieno[3,4-c][1,2,5]thiadiazole derivatives for photovoltaic applications

Two new donor-acceptor narrow-band-gap photovoltaic copolymers containing various electron-acceptor functional groups, such as thienopyrazine and thienodithiazole derivatives, are synthesized under the conditions of the Suzuki polycondensation reaction and characterized via ¹H NMR spectroscopy and GPC. The optical, electrochemical, and photovoltaic properties of the polymers are examined in detail. Both copolymers have good solubilities, high thermal stabilities, broad absorption regions (350–950 nm), relatively low levels of the highest occupied molecular orbital (?5.01 and ?5.02 eV for polymers I and II, respectively), and narrow band gaps (1.31 and 1.41 eV, respectively). Photovoltaic devices based on a polymer-II-PC₆₀BM (1: 3, wt/wt) mixture under AM 1.5 irradiation of 100 mV/cm² exhibit a power-conversion efficiency of ～0.29%, a short-circuit current of 1.45 mA/cm², an open-circuit voltage of V _oc = 0.67 V, and a fill factor of 0.30. These results are evidence that thienopyrazine functional groups are attractive as electron-acceptor building blocks in organic electronics.     

A Convenient Synthetic Entry Into 2,2-Diorganyl-5,6-Diaryl-1,3,4,2-Dioxaza Silacyclohexene Derivatives VIA Dianion Cyclisation: Sequential One-Pot Cyclosylation

In a convenient one-pot sequence, treatment of bezoin and p-anisoin oximes with sodium hydride in dry THF in 1:2 molar ratio generates 1,5-dianion, which upon subsequent addition of diorganodichlorosilane yields 1,3,4,2-dioxazasilacyclohexene derivatives in good yields. In general, very often a salt elimination route is used for the synthesis of the title compounds.     

Montmorillonite K-10 Clay Catalysed Glycosidation of 1-O-Acetyl-2,3-dideoxy-dl-pent-2-enopyrano-4-ulose

The O-glycosidation reaction of 1-O-acetyl-2,3-dideoxy-DL-pent-2-enopyran - 4 -ulose catalysed by the environmentally accepted and inexpensive industrial catalyst Montmorillonite K-10 clay with variety of alcohols in high yield is reported.     

Novel Carbon–Carbon Bond Formation between N‐Methyl‐3‐phenyl‐3‐hydroxypropylamine and Cresols Catalyzed by p‐Toluenesulphonic Acid

The p‐toluenesulphonic acid–catalyzed reaction between appropriate cresols and N‐methyl‐3‐phenyl‐3‐hydroxypropylamine in refluxing toluene resulted in the formation of o‐substituted phenol derivatives by an aromatic nucleophilic substitution reaction.     

Convenient and Scalable Synthesis of 2,3-Dihydroquinazolin-4(1H)-one Derivatives and Their Anticancer Activities

An efficient and mild InBr₃-catalyzed approach to synthesize 2,3-dihydroquinazolin-4(1H)-one derivatives (3a–3aa) has been developed. Notably, all the products were isolated by recrystallization and the reaction is accessible on a gram scale. Moreover, the reactions only require 10–60 min. All the synthesized compounds were evaluated for their in vitro anticancer activity against four human cancer cell lines.     

Copper(II) Bromide–Catalyzed C-C/C-N Bond-Forming Reactions: Synthesis of Pyrrole-Incorporated Triarylmethanes

We have achieved a facile copper(II) bromide–catalyzed synthesis of 2,3,4-trisubtitued pyrrole incorporated into unsymmetrical triarylmethanes through direct replacement of hydroxyl group in the pyrrolyl phenyl methanol with electron-rich aromatic and heteroaromatic compounds. The newly developed method has been applied to a facile synthesis of a C2 symmetric bis-triarylmethane in which the two triarylmethanes were bridged through piperzine. The copper(II) bromide catalysis led to C-C bond formation at the C(5) position when the reacting partner was imidazole. In contrast, C-N bond formation took place with benzimdazole or 2-methylbenzimidazole.     

Efficient Method for Demethylation of Aryl Methyl Ether Using Aliquat-336

A rapid method for selective cleavage of aryl methylethers can be achieved in the presence of a protic acid and a catalytic amount of phase-transfer catalyst (Aliquat-336). Aliquat-336 accelerates the rate of reaction and affords the corresponding phenols in excellent to good yields on a wide variety of substrates.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]     

Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); a new ‘metal free’ life for the Rupe rearrangement

A mild and selective transition metal free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Brønsted acidic ionic liquid [BMIM-SO₃H][OTf] as catalyst and [BMIM][PF₆] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov sequence utilizing this protocol has also been demonstrated.     

Surface and Antimicrobial Properties of N-Palmitoyl Amino Acid–Based Surfactants

Synthesized sodium N-pamitoyl amino acids were evaluated for surface and antimicrobial properties and compared with sodium lauryl sulfate (SLS). Emulsion stability of the amino acid surfactants and calcium tolerance of the sodium N-palmitoyl isoleucine were better as compared to SLS. Wetting ability and foaming properties of the palmitic acid-based surfactants were inferior to SLS. N-Acyl amino acids exhibited better antibacterial activity compared to sodium salts of N-acyl amino acids and standard compounds against Staphylococcus aureus MLS-16 and Bacillus subtilis. These studies revealed that the palmitoyl amino acid surfactants can be exploited in household, skin care formulations, and industrial applications.