Synthesis and characterization of thiophene containing angular polycyclic aromatic hydrocarbons (PAHs) are studied. Bis(benzothieno) naphthalene 1 (BBTN-1) is synthesized by the coupling of methyl 3-bromothiophene-2-carboxylate with 1,5-bis(naphthalenylboronic acid) through Suzuki coupling, followed by the hydrolysis of the methyl esters. Ring closing step will proceed by formation of acid chlorides and Friedel-Crafts chemistry. Isomer, BBTN-2, is synthesized in the likewise manner. Alkylsilyl acetylene substituents are attached via organolithium chemistry for solution processability. This structure-property relationship study aims to enhance the stability and performance of angular PAHs in electronic devices by the presence of additional Clar structures, relative to bistetracene. Results of this investigation may open new opportunities to explore these materials in mainstream applications such as bulk heterojunction solar cells and large-area, roll to roll solution processable transistors.<br/>Synthetic steps are confirmed via NMR and FTIR. Molecular packing motifs and crystal orientation is characterized via x-ray crystallography and x-ray diffraction, respectively. UV-vis spectroscopy, circular voltammetry, and ultraviolet photoelectron spectroscopy are utilized to investigate electronic structure. Target molecules are implemented into OFETs and OPVs to analyze device performance as well. Thermal properties are determined using TGA and DSC.

Design and synthesis of stable angular polycyclic aromatic hydrocarbons

249th National Meeting (2015)

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