Styryl dyes – synthesis and applications during the last 15 years

Abstract

One of the most widely used and important groups of functional dyes are the styryl dyes and a review of this functional dye class has not been published for more than 15 years. In this review article, we describe the new trends in the synthesis of a range of novel intermediates and styryl dyes and include the most interesting examples of their high‐tech applications. However, this review is not intended to be comprehensive because of the large number of styryl dye studies that have been carried out in this time. Styryl cyanine dyes are widely used in optical recording media in laser discs, as flexible dyes, laser dyes, as optical sensitisers and in various other fields, for example dye‐sensitised solar cells and dyes with non‐linear optical properties. Additionally, the most important applications for these dyes are in bio‐labelling and in medicinal analysis.

Arylstyrylimidazo[1,2-a]pyridine-based donor–acceptor acidochromic fluorophores: Synthesis, photophysical, thermal and biological properties

“…Table 1 In addition, the compounds 5e-h exhibit one shoulder at long wavelength in toulene used. The dyes which have two absorption bands or one absorption band with shoulder, may exhibit E-Z isomerization [27].…”

Studies of 2-azaazulenium derivatives – 3: The nature of electron transitions and spectral properties of styryl dyes containing terminal groups of different types

“…Yield 0.52 g (62%); m.p. 297-300°C (decomposition); 1 2-[2-(4-methoxyphenyl)vinyl]-1,3-dimethyl-1H-3,1-benzimidazol -3-ium iodide BIm-OMe. A mixture of 1,2,3-trimethyl-1H-3,1-benzimidazol-3-ium iodide (0.58 g, 2 mmol), p-anisaldehyde (0.544 g, 4 mmol) and piperidine (0.1 g) was heated in pyridine (7 mL) at 130°C for 8 h. Then p-anisaldehyde (0.27 g, 2 mmol) was added, and the heating was continued for 6 h. After cooling the precipitate was filtered off, washed with hot water (10 mL), ethanol (5 mL), diethyl ether (2 Â 5 mL), dried and purified by recrystallization from DMSO (twice).…”

“…1 H NMR spectra were recorded with spectral width 8000 Hz and numbers of points 32000; 13 C NMR spectra were recorded with spectral width 30,000 Hz and numbers of points 128,000. 1 HA 1 H COSY [18] spectra were acquired into 2048 (F2) and 512 (F1) time-domain data matrix and 2048 (F2) Â 2048 (F1) frequency-domain matrix after zero-filling.…”

“…Styryl dyes have numerous successful applications [1]. For example, they can be used as fluorescence probes, laser active and passive components, as optical sensitisers, as recording media (optical disks) and potential objects for molecular electronics.…”

Effective Stabilization of cis-Isomer of Styryl Dye inside the Cucurbit[7]uril Cavity

“…[25] Результаты и их обсуждение Стириловые красители являются одним из извест-ных классов органических фоточувствительных соеди-нений, которые находят широкое применение благо-даря своим уникальным оптическим свойствам. [26][27][28] Как известно, большинство стириловых производных вступают в различные фотохимические реакции под действием света. Наличие этиленовой С=С связи в структуре молекулы SP позволило предположить, что фотооблучение исследуемого раствора приведет к протеканию реакции фотоизомеризации.…”