Development of multifunctional organic materials is the current thirst area of research in organic materials chemistry. This study reports synthesis, crystal structure elucidation and multiple property investigation of E-3-pyridylvinyl benzoxazole (3-PVBO) and its methylated analogue, 3-MPVBO. With Z' = 2, 3-PVBO belongs to a rare class of crystals for which Z' > 1. Upon methylation, fascinating materials properties were observed. 3-[MPVBO]I exhibited strong emission and readily available redox states. It exhibited stronger emission at 474 nm with a larger Stokes shift of 8900 cm-1 compared to the emission of 3-PVBO at 386 nm with a Stokes shift of 5450 cm-1. Upon exposure to UV light, crystals of 3-PVBO underwent solid-state photodimerization reaction in a head-to-tail fashion leading to the formation of HT-rctt-isomer of the dimer, i.e., 1,3-bis(benzoxazole)-2,4-bis(3-pyridyl) cyclobutane (PBOCB). Herein, crystal structure, solid state photo-reactivity, and multiple materials properties, e.g., photophysical and electrochemical properties have been presented.

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