Simple Access to Sol–Gel Precursors Bearing Fluorescent Aromatic Core Units

Abstract

Di‐, tri‐, and tetrathienyl‐substituted polycyclic aromatic fluorophores were prepared from different aryldi‐, aryltri‐, or aryltetrahalides by a simple and fast Suzuki coupling. The reaction was optimized for the synthesis of the desired materials on multigram scale. The coupled products were converted into the corresponding iodides through iodination with N‐iodosuccinimide. The iodides turned out to be versatile starting materials for applications, such as periodic mesoporous organosilica syntheses. They were converted into a variety of new trimethoxysilyl arenes by using a very efficient Pd‐mediated C–Si cross‐coupling, which was also extended to the corresponding thienyl bromides by using a dimeric PdI catalyst. All compounds were characterized by 1H NMR, 13C NMR, 29Si NMR, and ATR‐IR spectroscopy and HRMS.

Oxidative Coupling of Methane: Opportunities for Microkinetic Model‐Assisted Process Implementations

“…As the dyes might potentially be relevant for OLED (organic light emitting diode) design, too,9 the analysis of the light emission by fluorescence is also of interest. The fluoresence spectra of all DTPTs consist of two bands: the main emission band at approximately 465 nm and a relatively intense preband in the range of 380–430 nm (Figure 9).…”

“…TiO 2 ) without changing the optical properties. For more significant changes to the optic properties, the dye between the two thiophenes would need to be replaced by other aromatic systems 9…”

Recent Developments in the Synthesis and Applications of 1,2,5-Thia- and Selenadiazoles. A Review

“…161 After in situ transmetallation with zinc chloride and a cross-coupling reaction with 4-iodoanisole, 4-bromo-7-(4-methoxyphenyl)benzo[c] [1,2,5]thiadiazole (139) was obtained in 58% yield (Scheme 68).…”

Alternating Tetrafluorobenzene and Thiophene Units by Direct Arylation for Organic Electronics

“…While the synthesis of fluorine‐free counterparts ( B‐3 , B‐5 , and B‐7 ) combining the advantages of divergent and convergent strategies, are shown in Scheme S1. These three oligomers were prepared by a standard Suzuki coupling reaction because of the lack of activating fluorine atoms on benzene . As the chain length increases, the solubility of the oligomers is less and less, whether in fluorine or fluorine‐free molecules.…”

“…These three oligomers were prepared by as tandard Suzuki coupling reaction because of the lack of activating fluorine atoms on benzene. [11] As the chain length increases, the solubility of the oligomers is less and less, whether in fluorineo r fluorine-free molecules. Therefore, both F-7 and B-7 just have limited solubility in common organic solvents.…”