138610-40-9Relevant articles and documents
Design and tuning of photoswitches for solar energy storage
Losantos, Raul,Sampedro, Diego
, (2021/07/09)
Current energy demand makes it compulsory to explore alternative energy sources be-yond fossil fuels. Molecular solar thermal (MOST) systems have been proposed as a suitable technology for the use and storage of solar energy. Compounds used for this application need to fulfil a long series of requirements, being the absorption of sunlight and the energy stored some of the most critical. In this paper, we study different families of well‐known molecular photoswitches from the point of view of their potential use as MOST. Starting from basic structures, we use density functional theory (DFT) computational modelling to propose two different strategies to increase the energy difference between isomers and to tune the absorption spectrum. The inclusion of a mechanical lock in the structure, via an alkyl chain and the presence of a hydrogen bonding are shown to di-rectly influence the energy difference and the absorption spectra. Results shown here prove that these two approaches could be relevant for the design of new compounds with improved performance for MOST applications.
Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry
Mendgen, Thomas,Steuer, Christian,Klein, Christian D.
supporting information; experimental part, p. 743 - 753 (2012/03/11)
Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.
(Z)-5-(2-Thienylmethylene)-2,4-imidazolidinedione
Gallucci, Judith C.,Mathur, Naresh,Shechter, Harold
, p. 1221 - 1223 (2007/10/02)
The major product formed in the termolysis of 5-diazouracil in thiophene at 423-433 K has been identified as the unexpected compound (Z)-5-(2-thienylmethylene)-2,4-imidazolidinedione, C8H6N2O2S, by X-ray analysis.The molecule is a hydantoin derivative with a thienylmethylene group substituted at the 5-position.The structure is disordered in that the thiophene ring exists in two orientations which are related by an approximate 180 deg rotation about the C(6)-C(7) bond.All of the N and O atoms are involved in an intermolecular hydrogen-bonding network via N-H...O interactions.This network consists of an infinite chain along the a-axis direction and a cyclic trimer arrangement which branches from this chain.The molecules are arranged in the unit cell in pleated sheets which are approximately perpendicular to the c-axis.
