3-Substituted 7-(diethylamino)coumarins as molecular scaffolds for the bottom-up self-assembly of solids with extensive π-stacking was written by Arcos-Ramos, Rafael;Maldonado-Dominguez, Mauricio;Ordonez-Hernandez, Javier;Romero-Avila, Margarita;Farfan, Norberto;Carreon-Castro, Maria del Pilar. And the article was included in Journal of Molecular Structure in 2017.Electric Literature of C14H14N2O2 This article mentions the following:
In this study, a set of mol. crystals derived from 3-substituted 7-(diethylamino)-2H-chromen-2-ones 1-8 were studied to sample the aggregation of coumarins into ordered solids. Crystals of parent compound 1a and its brominated derivative 2 were obtained and solved in the P-1 and C2/c space groups, resp. All the crystalline coumarins studied display extensive π-stacking in the solid-state. Theor. valence-conduction band gaps for derivatives 3b and 5 are close to crystalline rubrene, highlighting the importance of cooperativity and periodicity of π-stacking, in organic semiconductors; given their synthetic accessibility, electronic tunability and self-assembly via stacking, dipolar and H-bonding interactions, these systems arise as candidates for the bottom-up construction of organic crystals with extensive π-stacking and high polarizability. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Electric Literature of C14H14N2O2).
7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Electric Literature of C14H14N2O2
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts