200353-70-4Relevant articles and documents
The donor-acceptor biphenyl platform: A versatile chromophore for the engineering of highly efficient two-photon sensitive photoremovable protecting groups
Specht, Alexandre,Bolze, Frederic,Donato, Loic,Herbivo, Cyril,Charon, Sebastien,Warther, David,Gug, Sylvestre,Nicoud, Jean-Franois,Goeldner, Maurice
, p. 578 - 586 (2012)
Different photoremovable protecting groups in the o-nitrobenzyl, phenacyl, and 2-(o-nitrophenyl)propyl series with a donor-acceptor biphenyl backbone, known to display excellent two-photon absorption cross-sections, were investigated in order to develop efficient two-photon sensitive photoremovable protecting groups. The 2-(o-nitrophenyl)propyl series was a more versatile platform to increase the two-photon sensitivity of photoremovable protecting groups, leading to the p-alkoxy and p-bisalkylamino-4-nitro-[1,1′- biphenyl]-3-yl)propyl derivatives: PENB and EANBP respectively. Those two photoremovable protecting groups are to date the best caging groups for two-photon excitation at 800 and 740 nm respectively, offering attracting perspectives in chemical biology.
Crystal structure of 1-(2,4,6-trichlorobenzoyloxy) benzotriazole (TCB-OBt): observation of uncommon intermolecular oxygen-oxygen interaction and synthetic application in amidation
Dolai, Gobinda,Giri, Rajat Subhra,Mandal, Bhubaneswar,Roy, Sayanta,Sen, Srijit
, p. 19804 - 19811 (2021/11/12)
Herein, we investigated the supramolecular assembly of a modified Yamaguchi reagent TCB-OBt. Interestingly, each molecule is interconnected through novel chalcogen-chalcogen (O?O) interaction, π-π stacking, and aromatic C-H?O interaction. Hirshfeld surface analysis confirmed the existence of uncommon O?O interactions. A well-organized supramolecular layer structure and helical arrangement were observed in the crystal structure. TCB-OBt crystallized in the O-substituted desmotropic form. DFT calculations suggest that the O-substituted form is more stable than theN-substituted form (TCB-(N)-OBt). Morphology analysis indicates the formation of a fantastically well organized, continuous block-shaped system. Furthermore, the designed reagent works as an efficient activating reagent for amide bond formation with good yields under mild reaction conditions. Use of this reagent avoided intractable acid chlorides, and this new mixed-anhydride-based reagent may further be applicable for many other organic transformations.
Water-soluble, donor-acceptor biphenyl derivatives in the 2-(o-nitrophenyl)propyl series: Highly efficient two-photon uncaging of the neurotransmitter γ-aminobutyric acid at λ=800 nm
Donato, Loic,Mourot, Alexandre,Davenport, Christopher M.,Herbivo, Cyril,Warther, David,Leonard, Jeremie,Bolze, Frederic,Nicoud, Jean-Francois,Kramer, Richard H.,Goeldner, Maurice,Specht, Alexandre
supporting information; experimental part, p. 1840 - 1843 (2012/04/04)
Rattling the cage: The two γ-aminobutyric acid (GABA) derivatives 1 and 2 exhibit efficient and rapid (-6 s) GABA photorelease upon one-photon excitation combined with two-photon uncaging cross-section at λ=800 nm. Compounds 1 and 2 were