532930-53-3Relevant academic research and scientific papers
Incorporating cobalt carbonyl moieties onto ethynylthiophene-based dithienylcyclopentene switches. 1. Photochemistry
Harvey, Emma C.,Areephong, Jetsuda,Cafolla, Attilio A.,Long, Conor,Browne, Wesley R.,Feringa, Ben L.,Pryce, Mary T.
, p. 447 - 456 (2014)
The synthesis and characterization of a series of dithienyl perhydro- and perfluorocyclopentene photochromic molecular switches appended with cobalt carbonyl binding 3-ethynylthiophene and phenyl-3-ethynylthiophene substituents are reported. Their photochromic properties, fatigue resistance, and thermal stability were examined to establish the effect of substituents on their performance as molecular photoswitches. The photochemical properties of the dithienylethene core were retained to the greatest extent by the inclusion of phenyl units and a hexafluorocyclopentene ring. The alkyne units of the switches were used to coordinate cobalt carbonyl moieties: i.e., Co2(CO) 6 and Co2(CO)4(dppm). The cobalt carbonyl moieties were found to reduce the efficiency of cyclization and cycloreversion of the dithienylethene unit. Density functional theory was used to identify the excited states responsible for cyclization.
Photoswitching of bisthienylethene using 2D-π-A type pyran-based fluorescent dye for rewritable optical storage
Wang, Sheng,Qi, Qiaozhen,Li, Chengpeng,Ding, Guohua,Kim, Sung-Hoon
, p. 188 - 192 (2011)
The photoswitching of photochromic bisthienylethene mixed electron donor-π-accepter (2D-π-A) type fluorescent dye with appropriate doping ratio was constructed, which showed excellent fluorescence switch "on" and "off" when the photochromic bisthienylethe
Design, syntheses and photochromic properties of dithienylcyclopentene optical molecular switches
Yu, Chuanming,Hu, Bingcheng,Liu, Cheng,Li, Jiting
, (2016/12/22)
A kind of basal diarylethene through an easy synthetic procedure was synthesized and characterized, and a Suzuki coupling reaction was frequently operated to obtain the diarylethenes derivatives with some vivid functional groups like bromo, amido and pyridine. Two methods for derivatives of these switches contain porphyrins were described. All of their spectroscopic and photochromic properties were studied and intercompared. It is indicated that the difference in electron densities of the π-conjugated system of the closed forms has effects upon the absorption maxima in visible region of UV–Vis spectra. Dithienylcyclopentenes linked to porphyrins could emit luminescence substantially that display potentials to be used in the applications of nondestructive readout upon binary data storage and smart materials.
Synthesis of symmetrical and nonsymmetrical bisthienylcyclopentenes
Szaloki, Gyoergy,Pozzo, Jean-Luc
, p. 11124 - 11132 (2013/09/02)
Diarylethenes possess unique structural properties, which enabled them to find widespread applications in the field of photochromism. Nowadays, bisthienylcyclopentenes (BTCs) present the most popular subfamily of these compounds, which are widely used as P-type chromophores. This minireview summarises the main strategies for the synthesis of symmetrical and nonsymmetrical BTCs. In addition, attention is drawn to desymmetrisations achieved by monosubstitutions, which is not frequently utilised, although it can be highly advantageous. This is supported with some of the authors' latest results. Copyright
Photoresponsive dithienylethene-urea-based organogels with "reversed" behavior
Akazawa, Masako,Uchida, Kingo,De Jong, Jaap J. D.,Areephong, Jetsuda,Stuart, Marc,Caroli, Giuseppe,Browne, Wesley R.,Feringa, Ben L.
supporting information; experimental part, p. 1544 - 1547 (2008/10/09)
Dithienylperhydrocyclopentene-bisurea-based low molecular weight gelators are described that function as photoresponsive organogels that show a remarkable gel-to-liquid transition upon irradiation. The two series of derivatives, with and without alkyl spacers between the urea hydrogen bonding groups and the photochromic unit, show different gelation behavior. Upon UV irradiation of the gels, a gel liquified at only 1.4% conversion of the photochromic unit. Transmission electron microscopy (TEM) shows that the gel fibres consist of thin ribbons. Semi-empirical (PM3) calculations indicate that the hydrogen bonding between the open-ring isomer (o) molecules is weak, and that formation of the closed-ring isomer (c) destabilises the hydrogen bonding further. The results indicate that a small amount of the closed-ring isomer will disrupt the intermolecular hydrogen-bonding, leading to disintegration of the gel fibre ribbons and hence reversible liquification. The Royal Society of Chemistry 2008.
Molecular switches get wired: Synthesis of diarylethenes containing one or two sulphurs
Kudernac,De Jong,Van Esch,Feringa,Dulic,Van Der Molen,Van Wees
, p. 205 - 210 (2007/10/03)
Two series of novel diarylethenes, the first containing one and the second two acetyl protected thiol groups, were synthesised in two and three steps from an easily available known intermediate. Newly synthesised compounds present ideal examples of model
Photochromic properties of perhydro- and perfluorodithienylcyclopentene molecular switches
De Jong, Jaap J. D.,Lucas, Linda N.,Hania, Ralph,Pugzlys, Audrius,Kellogg, Richard M.,Feringa, Ben L.,Duppen, Koos,Van Esch, Jan H.
, p. 1887 - 1893 (2007/10/03)
Various substituted phenylthienyl perhydro- and perfluorocyclopentenes have been synthesized in order to compare their spectroscopic and photochromic properties. The difference in the electron densities of the central cyclopentene moieties in the perhydrocyclopentene and perfluorocyclopentene molecular switches has only a small effect on the absorption maxima of the electronic spectra, but causes some subtle changes in substituent and solvatochromic effects. The photochromic behaviour is remarkably similar, and both type of switches combine excellent quantum yields (0.6) with high degrees of photoconversion (> 0.85). The main difference is the lower photochemical and thermal stability of the perhydrocyclopentene molecular switches. It is concluded that in most studies the perhydrocyclopentenes are an excellent alternative for the perfluorocyclopentenes, while the perfluorocyclopentenes might be better suited for applications such as data storage, which depend critically on fatigue resistance and thermal stability. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
