500772-41-8

Upstream product

• 960-16-7 tributylphenylstannane 
• 500772-34-9 2-bromo-3,5-dimethyl-dithieno[2,3-d:3',2'-b]thiophene-4,4-dioxide 
• 30318-99-1 3-bromo-4-methylthiophene 
• 379692-12-3 bis(4-methylthiophen-3-yl)sulfide 

Downstream Products

• 1345692-49-0 2-phenyl-6-(thiophen-2-ylmethanol)-3,5-dimethyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide 
• 1345692-48-9 2-phenyl-6-(2-(2-((2-methoxyethoxy)methoxy)ethyl)thiophene)-3,5-dimethyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide 
• 1345692-47-8 2-phenyl-6-(2-methylthiophene)-3,5-dimethyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide 
• 500772-43-0 2-phenyl-3,5-dimethyl-6-[(4-dimethyl(chloromethyl)silyl)phenyl]dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide 
• 500772-42-9 2-bromo-3,5-dimethyl-6-phenyl-dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide 

Relevant academic research and scientific papers

Live-cell-permeant thiophene fluorophores and cell-mediated formation of fluorescent fibrils

In our search for thiophene fluorophores that can overcome the limits of currently available organic dyes in live-cell staining, we synthesized biocompatible dithienothiophene-S,S-dioxide derivatives (DTTOs) that were spontaneously taken up by live mouse embryonic fibroblasts and HeLa cells. Upon treatment with DTTOs, the cells secreted nanostructured fluorescent fibrils, while cell viability remained unaltered. Comparison with the behavior of other cell-permeant, newly synthesized thiophene fluorophores showed that the formation of fluorescent fibrils was peculiar to DTTO dyes. Laser scanning confocal microscopy of the fluorescent fibrils showed that most of them were characterized by helical supramolecular organization. Electrophoretic analysis and theoretical calculations suggested that the DTTOs were selectively recognized by the HyPro component of procollagen polypeptide chains and incorporated through the formation of multiple H-bondings.

Rigid-core fluorescent oligothiophene-S,S-dioxide isothiocyanates. Synthesis, optical characterization, and conjugation to monoclonal antibodies

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.