NOVEL CHROMOPHORES BASED ON CLOSED-SHELL AND OPEN-SHELL POLYCYCLIC AROMATIC HYDROCARBONS

Abstract

The thesis demonstrated the design and synthesis of novel chromophores based on functionalized polycyclic aromatic hydrocarbons (PAHs) and stable open-shell PAHs with tunable electronic ground state. Their promising properties and related applications were also investigated. For functionalized PAHs, the novel C3 symmetric hexa-peri-hexa benzocoronene chromophores (HBC-NO2, HBC-CN, HBC-CF3, and HBC-COOH) have been prepared for the first time. Remarkable two photon absorption responses and optical power limiting performances were achieved for octupolar HBC derivatives. All these disc-like molecules self-assembed into two-dimensional network at solid-liquid interface via dipole-dipole or hydrogen -bonding interactions. For open-shell PAHs, new stable benzannulated Chichibabin¿s hydrocarbons (1-CS and 2-OS) and quinoidal rylenes (Per-CN, 2Per-CN, QDTP and QDTQ) with tunable ground electronic state were successfully synthesized and their geometry in the ground state were investigated by various experiments. These work established a new approach to design stable open-shell PAHs and also provided reliable characterization methods.