Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes

Abstract

The synthesis, experimental and theoretical study of the novel air-stable four adamantane-bearing dyes based on the transepindolidione (EPI) and trans-quinacridone (QA) cores are presented. Compared to the parent EPI and QA, the methyl-/ ethyladamantyl substitution ensures that their structural stability in crystals is preserved due to the self-organizing properties of adamantyl groups. The investigated materials are solutionprocessable in common organic solvents and possess excellent thermal stability. The very good solubility was achieved by a one-step short and easy synthesis, which resulted in moderate yields of a new family of synthesized dyes. The ethyladamantyl EPI derivative (3) exhibits a unique rise in thermal stability reaching 412 °C. The resulting electrochemical band gap carried out on thin-film evaporated on ITO-coated glass electrodes was in the range of 2.4-2.5 eV. The experimental HOMO energies range from À 6.2 to À 6.0 eV, and LUMO energies lay between À 3.7 and À 3.5 eV. The prepared compounds are characterized by strong fluorescence in solutions and in powder, suggesting a decrease in the extent of non-radiative relaxation processes.

Hydrogen Bonding Nanoarchitectonics of Organic Pigment-Based Janus Microrobots with Entering Capability into Cancer Cells

“…The common feature of this class of pigment is their ability to organize due to the formation of intermolecular hydrogen bonds and π–π interactions. Intermolecular interactions make these materials robust and abundant, with excellent stability compared to common organic dyes. , Moreover, these materials possess semiconductive and photocatalytic properties , that can be further adjusted by side chain modifications. , In addition, the availability of N–H groups on the surface of hydrogen-bonded pigments allows their bioconjugation with functional biomolecules, making them attractive for bio-oriented applications. , In a study by Sytnyk and co-workers, the organic pigment microcrystal films were proven to attach to cells, making them grow in direct contact without causing them any harm. The optoelectrical properties of organic pigments enabled the photostimulation of cells through the tight interface.…”

“…35,36 Moreover, these materials possess semiconductive and photocatalytic properties 38,39 that can be further adjusted by side chain modifications. 40,41 In addition, the availability of N−H groups on the surface of hydrogen-bonded pigments allows their bioconjugation with functional biomolecules, making them attractive for bio-oriented applications. 36,42 In a study by Sytnyk and co-workers, 43 the organic pigment microcrystal films were proven to attach to cells, making them grow in direct contact without causing them any harm.…”