19698-46-5Relevant articles and documents
Rewiring chemistry: Algorithmic discovery and experimental validation of one-pot reactions in the network of organic chemistry
Gothard, Chris M.,Soh, Siowling,Gothard, Nosheen A.,Kowalczyk, Bartlomiej,Wei, Yanhu,Baytekin, Bilge,Grzybowski, Bartosz A.
, p. 7922 - 7927 (2012/09/08)
Computational algorithms are used to identify sequences of reactions that can be performed in one pot. These predictions are based on over 86 000 chemical criteria by which the putative sequences are evaluated. The "raw" algorithmic output is then validated experimentally by performing multiple two-, three-, and even four-step sequences. These sequences "rewire" synthetic pathways around popular and/or important small molecules. Copyright
Rigid-core fluorescent oligothiophene-S,S-dioxide isothiocyanates. Synthesis, optical characterization, and conjugation to monoclonal antibodies
Sotgiu, Giovanna,Zambianchi, Massimo,Barbarella, Giovanna,Aruffo, Fabio,Cipriani, Franco,Ventola, Alfredo
, p. 1512 - 1520 (2007/10/03)
In this paper we report the synthesis of a new class of fluorescent thiophene-based isothiocyanates containing a 3,5-disubstituted dithieno [3,2-b:2′,3′-d] thiophene-4,4-dioxide moiety as the rigid core, using the palladium-catalyzed cross-coupling reaction of aryl stannanes with aryl bromides (Stille coupling). By changing the molecular structure through the progressive addition of thienylene or phenylene units, light emission from blue to orange was obtained. Photoluminescence quantum yields ranged from 0.65 to 0.90 for blue and green light emitters to 0.10-0.35 for yellow and orange ones. Optically and chemically stable fluorescent bioconjugates were prepared by spontaneous reaction of the isothiocyanates with monoclonal antibodies anti-CD3 and anti-CD8 in slightly basic solutions.
Synthesis, characterization, and electrogenerated chemiluminescence of phenyl-substituted, phenyl-annulated, and spirofluorenyl-bridged oligothiophenes
Mitschke, Ullrich,Baeuerle, Peter
, p. 740 - 753 (2007/10/03)
To overcome the insolubility of higher oligothiophenes and simultaneously to enhance their processability with respect to an application in molecularly doped organic light-emitting devices (OLEDs) we synthesized phenyl-substituted, phenyl-annulated, and spirofluorenyl-bridged oligothiophenes 1-5. Significantly improved solubilities in polar solvents of up to three orders of magnitude were found and their optical and electrochemical properties were investigated in solution. Reflecting small conformational changes and the almost complete electronic separation of the substituents, phenyl substitution and the introduction of a spiro core by bridging the central bithienyl unit only slightly affected optical and redox properties in comparison to the unmodified oligothiophenes (6-8). In contrast, the presence of an isothianaphthene (benzo[c]thiophene) unit in the oligomeric chain led to a distinct approximation of the frontier orbitals and consequently to a red-shift of both absorption and fluorescence. Finally, we demonstrated the applicability of some oligomers as dopants for OLEDs by electrogenerated chemiluminescence (ECL).
