820972-68-7

Usage

Uses

Used in Organic Synthesis:
4-(TERT-BUTYLSULFANYL)PHENYLBORONIC ACID is used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity and functional groups allow for the formation of new chemical bonds and the creation of complex molecules with diverse applications.
Used in Functionalization of Photoswitches:
In the field of photochemistry, 4-(TERT-BUTYLSULFANYL)PHENYLBORONIC ACID is used as a functionalization agent for tetrahydronaphtho[2,1-a]azulene photoswitches. Its incorporation into these photoswitches enhances their photophysical properties, enabling reversible and efficient control of their molecular structures and functions upon exposure to light. This makes it a promising candidate for applications in molecular switches, sensors, and other optoelectronic devices.

Upstream product

• 25752-90-3 tert-butyl 4-bromophenyl sulfide 
• 121-43-7 Trimethyl borate 

Downstream Products

• 1430198-68-7 7-[4-(tert-butylthio)phenyl]-2-phenyl-1,8a-dihydroazulene-1,1-dicarbonitrile 

Relevant academic research and scientific papers

Biphenyl Sulfonic and Disulfonic Acids with Perfluorinated Alkyl Residues

Sulfonic acids serve as interesting, yet not intensively studied alternatives to carboxylic acids as linker units in coordination polymers. In this study, we present the synthesis of hybrid sulfonic acids with polar, rigid biphenyl moieties and disordered highly fluorinated alkyl chains. Consequently, eight biphenyl sulfonic and disulfonic acids with one or two perfluoroalkyl chains were prepared. The key steps within the synthesis include two palladium catalyzed C–C bond formations: The perfluoroalkyl residue is installed by Heck reaction (up to 91 %) using 1H,1H,2H-perfluorinated alkenes (C6 and C8) and the biphenyl unit is established by a Suzuki coupling (up to 88 %) of boronic acids bearing one or two protected thiol groups. Finally, these thiol groups are converted into the sulfonic acids by N-chlorosuccinimide mediated oxidation followed by hydrolysis of the respective sulfonyl chloride.

Synthesis and properties of functionalized oligo(arylene) molecular wires with thiolated termini: Competing thiol-au and nitro-au assembly

(Chemical Presented) We report the synthesis by Suzuki cross-coupling methodology of oligo(arylene) molecular wires with protected thiolates at both termini and a central electron-acceptor unit (3,5-dinitrofluorenone, compounds 10-12) or an electron-donor unit [9-(1,3-dithiol-2-ylidene)fluorene, compounds 14-17] in the backbone. Core reagents are 2,7-dibromo-3,5-dinitrofluorenone 7 (obtained by nitration of 2,7-dibromofluorenone) and 2,7-dibromo-9-(4,5- dimethyl-1,3-dithiol-2-ylidene)fluorene 13. The solution electrochemical redox properties of these oligo(arylene) derivatives have been studied. The reduction CVs of the dinitrofluorenone-containing molecules display three reversible/quasireversible couples yielding, sequentially, radical anion, dianion, and radical trianion species, e.g., for 11 E1red -1.02 V (vs. Ag/Ag+ in THF). The 1,3-dithiol-2-ylidene unit imparts good electron donor properties tomolecules 14, 15, and 16 with radical cation formation observed at Eox ca. 0.65 V (vs. Ag/Ag+ in DCM). We also report studies on the assembly of 11 and 15 on gold substrates. Current-voltage (I-V) characteristics and X-ray photoelectron spectra of the monolayers reveal that 11 assembles via competing S-Au and NO2-Au interactions. This unusual phenomenon is ascribed to the very electron deficient dinitrofluorenone core of 11 weakening the S-Au interaction. An important conclusion is that thiolated molecules which possess strongly electron-withdrawing core units, especially those containing nitro groups, may not be suitable for controlled assembly in junctions. In contrast, 15 assembles via conventional S-Au interactions.