ISBN 9783843921671

978-3-8439-2167-1, Reihe Organische Chemie

Markus Gantenbein
Small Organic Molecules: Building Blocks of Functional Materials

176 Seiten, Dissertation (2015), Softcover, A5

Zusammenfassung / Abstract

The potential of phosphorescent organic light emitting diodes (phOLEDs) in full-color flat-panel display solid state lighting devices is fueling the interest in high triplet energy materials.

The design of blue pixel host materials is based on the idea of reducing the level of conjugation between the carbazole subunit and the biphenyl backbone. Therefore, a series of CBP derivatives was synthesized and studied with spatially restricted degrees of freedom in their biphenyl-N-carbazole junctions by introducing spatial demanding methyl moieties either in positions 1 and 8 of the carbazole unit or in positions 3,5,3’,5’ of the biphenyl backbone. Moreover, the electronic features of the carbazole synthons were investigated by attaching electron-withdrawing or electron-donating groups in the positions 3 and 6 or positions 2 and 7 of the carbazole subunits.

Acetylenes are highly intriguing building blocks in molecular electronics. Besides their modularity, synthetic accessibility and efficient post-functionalization by click-chemistry, acetylenes allow a broad scope of protecting groups that makes them ideally suited for targeted assembly of multifunctional self-assembled monolayers (SAMs). The idea of an electrochemically-triggered deprotection of acetylene enables the specific addressability of the desired reaction site. When this deprotection of the immobilized acetylene takes place on a conductive surface, post-functionalization leads to the formation of a multifunctional SAM.

The progress towards the synthesis of a ball-shaped, highly symmetric thiospherophane is discussed. This ball-shaped molecule consists of eight identical benzene subunits, which are interconnected via a sulfur atom. The insertion of these sulfur heteroatoms would transform the fullerene closed-shell structure into a hollow molecular cage