1284751-09-2

Upstream product

• 121-43-7 Trimethyl borate 
• 939-97-9 4-tert-Butylbenzaldehyde 

Downstream Products

• 1620789-21-0 C₂₆H₂₃NO 
• 1620789-23-2 C₂₇H₂₃N 

Relevant academic research and scientific papers

1,8,10-Trisubstituted anthracenyl hydrocarbons: Towards versatile scaffolds for multiple-H-bonded recognition arrays

In this work, we describe the synthesis of 1,8,10-trisubstituted anthracenyl scaffolds that, bearing boronic acid functionalities, can act as multiple H-bonding donor systems. The trisubstituted anthracenyl derivatives are synthesized following two main synthetic pathways. Whereas in the first approach trisubstituted anthracenyl derivatives are prepared through the regioselective addition of the relevant organomagnesium nucleophile to 1,8-dichloroanthraquinone, in the second avenue a triflate-bearing anthracene is prepared by reduction of the anthraquinone into the anthrone precursor and functionalized through metal-catalysed cross-coupling reactions. Complementary studies of the Na2S2O4-mediated reduction of 1,8-dichloroanthraquinone allowed to shed further light on the possible mechanism of formation of the anthrone precursor, suggesting the presence of a cis-diol intermediate undergoing antiperiplanar elimination. Solid-state X-ray diffraction investigations of the bisboronic acids show that the molecules self-assemble into dimers through the formation of four H-bonds established between the anti-syn conformers of the boronic acid moieties. 1H-NMR titrations between bisboronic acids and tetra H-bond acceptor, diisoquinolino-naphthyridine, showed a significant shift of the -B(OH)2 proton resonances, suggesting the presence of H-bonding interactions between both molecules.

An AAAA-DDDD quadruple hydrogen-bond array

Secondary electrostatic interactions between adjacent hydrogen bonds can have a significant effect on the stability of a supramolecular complex. In theory, the binding strength should be maximized if all the hydrogen-bond donors (D) are on one component and all the hydrogen-bond acceptors (A) are on the other. Here, we describe a readily accessible AAAA-DDDD quadruple hydrogen-bonding array that exhibits exceptionally strong binding for a small-molecule hydrogen-bonded complex in a range of different solvents (K a>3 × 1012 M-1 in CH 2Cl2, 1.5 × 106 M-1 in CH 3CN and 3.4 × 105 M-1 in 10% v/v DMSO/CHCl3). The association constant in CH2Cl2 corresponds to a binding free energy (ΔG) in excess of -71 kJ mol -1 (more than 20% of the thermodynamic stability of a carbon-carbon covalent bond), which is remarkable for a supramolecular complex held together by just four intercomponent hydrogen bonds.

IRIDIUM COMPLEX AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

The present invention provides a novel iridium complex and an organic light-emitting device including the novel iridium complex. The novel iridium complex includes three ligands, and two of them have a phenyl-naphtho[2,1-f]isoquinoline skeleton. The prese