Specialized side chain influence on arrangement of conjugated macromolecules in organic electronics
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Specialized side chain influence on arrangement of conjugated macromolecules in organic electronics Theodore Hicks 171 Pages Directed by Dr. Seth R. Marder This dissertation focuses on the design, synthesis, and characterization of pi-conjugated small molecules and 2D polymers of potential interest for organic electronic applications. An investigation of the structure-property relationships that effect two different classes of conjugated macromolecules, covalent organic frameworks (COFs) and small-molecule electron acceptors, is conducted by synthesis of new materials and characterization of the resulting optical, electronic and physical properties. Chapter 2 describes two different approaches toward development of a generalizable method for synthesizing 2D crystalline polymer monolayers. The findings include a remarkable tolerance of interlayer stacking in imine-linked COFs composed of isoindigo as well as the development of air-water polymerization methods to generate monolayer films. The characteristics of the COF materials are demonstrated using a variety of spectroscopic and microscopy techniques. Chapter 3 details the synthesis and characterization of small molecules designed for use in organic photovoltaics. The new compounds are evaluated for electronic and optical suitability before incorporation into test devices. Chapter 4 gives a perspective on the impact of synthetic complexity on organic electronic devices and contains an investigation of new synthetic methods based on ultra-efficient catalysis of precursors required for organic semiconductors.