107938-07-8

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 98-80-6 phenylboronic acid 
• 308255-23-4 2-(3-bromo-5-phenylthiophen-2-yl)[1,3]dioxolane 
• 23688-07-5 3,5-dibromo-2-thiophenecarboxaldehyde 
• 71-43-2 benzene 

Downstream Products

• 1174879-60-7 (3-bromo-5-phenylthiophen-2-yl)methanol 
• 35022-09-4 2-phenylthieno<3,2-b>thiophene 

Relevant academic research and scientific papers

Acid-base-responsive intense charge-transfer emission in donor-acceptor-conjugated fluorophores

Herein we report on the synthesis and acid-responsive emission properties of donor-acceptor (D-A) molecules that contain a thienothiophene unit. 2-Arylthieno[3,2-b]thiophenes were conjugated with an N-methylbenzimidazole unit to form acid-responsive D-A-t

The photochromic and self-assembling properties of diarylethenes having chiral amphiphilic chains at the reactive carbon atoms

A photochromic diarylethene derivative having chiral polyethylene glycol side chains at the reactive carbon atoms was synthesized. The diarylethene showed a photochromic reaction upon irradiation with UV and visible light in both ethyl acetate and water.

PHOTOCHEMICAL ARYLATION OF FURANS AND THIOPHENES

The photochemical behaviour of furan and thiophene is discussed with special attention to photoarylation of thiophene.The irradiation of 5-bromofuran-2-carbaldehyde, 41, in benzene gave good yields of the corresponding 5-phenyl derivative 42.The reaction 41--->42 has been studied considering the photochemical behaviour changing both the position of the halogen on the furan ring and the effect of the solvent.Kinetic and spectroscopic data are in agreement with the formation of a transient triplet exciplex in this type of reactions.The use of both the iodo derivative 50 and acetonitrile as solvent allowed the conversion to be optimized.On the contrary, the irradiation of 41 in diethyl ether or in an amine furnished the dehalogenation product 53.Photoarylation can be extended to thiophene derivatives and aromatic or heteroaromatic donors.The reaction also occurs with halothiophenes or thiazoles as donors, or by using halothiophene carboesters as acceptors.On the contrary, halothiophene carbonitriles are unreactive under similar conditions.Some applications to the synthesis of naturally occurring polythiophenes are reported.The target compounds were obtained through photoarylation and subsequent reaction with alkynes in the presence of palladium(0) complexes as catalysts.The role of polythiophenes in the environment is discussed.The hypothesis that the bioactivity of these compounds is related to the capability to be singlet-oxygen sensitizers is supported by the finding that all the bithiophenes synthesized are singlet-oxygen sensitizers.

Photochemical Synthesis of Phenyl-2-thienyl Derivatives

The irradiation (in benzene solution) of 5-bromo- and 5-iodo-thiophene-2-carbaldehyde or the corresponding methyl ketones furnishes the corresponding 5-phenyl derivatives.The same reactivity for other halogenothiophenes is reported: 3,5-dibromothiophene-2-carbaldehyde furnishes the 3-bromo-5-phenyl-2-thienyl derivative while the corresponding di-iodo compound yields 3,5-diphenylthiophene-2-carbaldehyde.In contrast, 5-acetyl-2,3-di-iodothiophene furnishes only the photosubstitution pruduct at C-5.Generally the iodine-containing compounds are more reactive and more stable under the reaction conditions than ones bearing bromine, in agreement with previous reports on the corresponding furan photochemistry.