“…The results obtained indicate the formation of angular 2,6-diphenylbenzo[1,2-d:4,3-d′]bis(thiazole) 9a (see SI). The IR spectral data and physical constants of compound 9a coincide with those previously described in the literature. , …”
This article focuses on the development of practical approaches to the preparation of benzo[1,2-d:4,3-d′]bis(thiazoles) using blue light-induced photochemical cyclization of N,N′-(1,4-aryl)dithioamides in the presence of p-chloranil as a mild oxidant. The proposed method allows to obtain benzo[1,2-d:4,3-d′]bis(thiazoles) containing donor substituents in the conjugated chain. Photophysical and (spectro)electrochemical properties of 2,6-di([2,2′-bithiophen]-5-yl)benzo[1,2-d:4,3-d′]bis(thiazole) and -benzo[1,2-d:4,5-d′]bis(thiazole) are studied in detail. The properties of the synthesized compounds suggest their potential applications for organic electronics.
“…The results obtained indicate the formation of angular 2,6-diphenylbenzo[1,2-d:4,3-d′]bis(thiazole) 9a (see SI). The IR spectral data and physical constants of compound 9a coincide with those previously described in the literature. , …”
This article focuses on the development of practical approaches to the preparation of benzo[1,2-d:4,3-d′]bis(thiazoles) using blue light-induced photochemical cyclization of N,N′-(1,4-aryl)dithioamides in the presence of p-chloranil as a mild oxidant. The proposed method allows to obtain benzo[1,2-d:4,3-d′]bis(thiazoles) containing donor substituents in the conjugated chain. Photophysical and (spectro)electrochemical properties of 2,6-di([2,2′-bithiophen]-5-yl)benzo[1,2-d:4,3-d′]bis(thiazole) and -benzo[1,2-d:4,5-d′]bis(thiazole) are studied in detail. The properties of the synthesized compounds suggest their potential applications for organic electronics.
“…The more extensive conjugation in 2 shifts its LAB bathochromically relative to that of the monostyrylcrown ether analogue 1 . Such shifts for bischromophoric compounds have been reported previously …”
Section: Resultssupporting
confidence: 80%
“…Synthesis. The bisheterocyclic compound 2,5-dimethylbenzobis(thiazole) 3 was obtained in three steps as described earlier. , The target compound 2 was prepared by condensation of 3 with 4‘-formyl-2,3-benzo-15-crown-5 ether in the presence of t- BuOK in DMF at ambient temperature (Scheme ). 1 Aromatic and olefinic region of the 1 H NMR spectrum of 2 in DMSO- d 6 , 25 °C, 500 Hz. 2 …”
Section: Resultsmentioning
confidence: 99%
“…Potassium tert -butoxide ( t- BuOK) was prepared by dissolution of the alkali metal in anhydrous t- BuOH, evaporation of excess alcohol, and drying of the salt in vacuo. Preparations of N -(3-acetylaminophenyl)acetamide, N -(3-thioacetylaminophenyl)acetamide, and 2,7-dimethylbenzo[1,2- d ,3,4- d ‘]bisthiazole were as described earlier. , …”
2,7-Bis[2-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxabenzocyclopentadecen-2-yl)vinyl]-benzo[1,2-d;3,4-d']bisthiazole, 2, with crown ether styryl moieties substituted on a heterocyclic core, was synthesized and its complex forming ability with several metal cations was evaluated in acetonitrile by absorption and fluorescence spectroscopy. The results are compared to those for the analogous ligand possessing a single crown ether styryl moiety. Selective binding of the metal cation at the heterocyclic core of both ligands was observed only for Hg2+. Alkali and alkaline earth cations bind selectively at the crown ether moieties. Stability constants and pure spectra of defined stoichiometry were determined with the use of HYPERQUAD, a least-squares fitting program, and the results were validated in one case by subjecting the titration spectral matrix to singular value decomposition with self-modeling (SVD-SM). The multitopic ligand 2 forms relatively strong 2:2 stoichiometric complexes with K+, among the alkali metal cations, and Ba2+, among the alkaline earth metal cations, and is a promising selective optical sensor for these ions.
“…Ac 2 O was efficient enough in the one-step formation of a benzobisthiazole scaffold and the use of orthoesters and rare-earth metal triflates as catalysts was not necessary, albeit the latter method provides the desired product in somewhat higher yield which was first reacted with KSCN and Br 2 to afford the thiocyanate 8 . This was consequently transformed in one pot to 3-Me via reduction with Na 2 S and ring-closing reaction between Ac 2 O and the intermediately formed 6-amino-2-methylbenzothiazol-7-thiol …”
A computer-aided design of novel D-π-A-π-D styrylamines containing five isomeric benzobisthiazole moieties as the electron-accepting core has revealed the linear centrosymmetric benzo[1,2-d:4,5-d']bisthiazole as the most promising building block for engineering chromophores displaying high two-photon absorption (TPA) in the near-IR region, as also confirmed experimentally. The ease of synthesis of quadrupolar derivatives thereof, combined with extraordinarly high TPA action cross sections (δTPAΦf > 1500 GM), makes these heteroaromatic systems particularly attractive as diagnostic agents in 3D fluorescence imaging.
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