5411-14-3Relevant articles and documents
(Trifluoromethylselenyl)methylchalcogenyl as Emerging Fluorinated Groups: Synthesis under Photoredox Catalysis and Determination of the Lipophilicity
Grollier, Kevin,De Zordo-Banliat, Arnaud,Bourdreux, Flavien,Pegot, Bruce,Dagousset, Guillaume,Magnier, Emmanuel,Billard, Thierry
supporting information, p. 6028 - 6033 (2021/03/15)
The synthesis of molecules bearing (trifluoromethylselenyl)methylchalcogenyl groups is described via an efficient two-step strategy based on a metal-free photoredox catalyzed decarboxylative trifluoromethylselenolation with good yields up to 88 %, which raised to 98 % in flow chemistry conditions. The flow methods allowed also to scale up the reaction. The mechanism of this key reaction was studied. The physicochemical characterization of these emerging groups was performed by determining their Hansch–Leo lipophilicity parameters with high values up to 2.24. This reaction was also extended to perfluoroalkylselenolation with yields up to 95 %. Finally, this method was successfully applied to the functionalization of relevant bioactive molecules such as tocopherol or estrone derivatives.
Triazole-amide isosteric pyridine-based supramolecular gelators in metal ion and biothiol sensing with excellent performance in adsorption of heavy metal ions and picric acid from water
Panja, Atanu,Ghosh, Kumaresh
, p. 934 - 945 (2019/01/09)
Pyridine-based small molecular gelators 1-4, having a triazole-amide isosteric relationship, have been synthesized. Compounds 1-3 exhibit excellent gelation from DMSO-H2O (1?:?2, v/v), while compound 4 forms a gel in the presence of Ag+ ions in DMSO-H2O (1?:?2, v/v). The change from triazole to isosteric amide has a marked effect on the gelling abilities, minimum gelation concentrations (mgc), thermal stability, mechanical properties, metal ion-responsive character and adsorption properties of the structures, as established by various techniques. All the gels have been successfully applied in sophisticated sensing kits for the selective detection of Cu2+ and Ag+ ions and thiol-containing amino acids. The triazole-based gelators 1 and 3 adsorb heavy metal ions from water with greater efficiency than the isosteric amide-based gelators. The metallogel 4-Ag+ can be used in the efficient removal of picric acid (a nitro explosive) from water.
Snapshotting the excited-state planarization of chemically locked N,N′-disubstituted dihydrodibenzo[a,c]phenazines
Chen, Wei,Chen, Chi-Lin,Zhang, Zhiyun,Chen, Yi-An,Chao, Wei-Chih,Su, Jianhua,Tian, He,Chou, Pi-Tai
supporting information, p. 1636 - 1644 (2017/02/10)
For deeper understanding of the coupling of electronic processes with conformational motions, we exploit a tailored strategy to harness the excited-state planarization of N,N′-disubstituted dihydrodibenzo[a,c]phenazines by halting the structural evolution via a macrocyclization process. In this new approach, 9,14-diphenyl-9,14-dihydrodibenzo[a,c]phenazine (DPAC) is used as a prototype, in which the para sites of 9,14-diphenyl are systematically enclosed by a dialkoxybenzene-alkyl-ester or-ether linkage with different chain lengths, imposing various degrees of constraint to impede the structural deformation. Accordingly, a series of DPAC-n (n = 1-8) derivatives were synthesized, in which n correlates with the alkyl length, such that the strength of the spatial constraint decreases as n increases. The structures of DPAC-1, DPAC-3, DPAC-4, and DPAC-8 were identified by the X-ray crystal analysis. As a result, despite nearly identical absorption spectra (onset ～400 nm) for DPAC-1-8, drastic chain-length dependent emission is observed, spanning from blue (n = 1, 2, ～400 nm) and blue-green (n = 3-5, 500-550 nm) to green-orange (n = 6) and red (n = 7, 8, ～610 nm) in various regular solvents. Comprehensive spectroscopic and dynamic studies, together with a computational approach, rationalized the associated excited-state structure responding to emission origin. Severing the linkage for DPAC-5 via lipase treatment releases the structural freedom and hence results in drastic changes of emission from blue-green (490 nm) to red (625 nm), showing the brightening prospect of these chemically locked DPAC-n in both fundamental studies and applications.
