New functionalized siloles have been synthesized and their optical characterizations are investigated. Silole unit has been interested, since silole has a unique optical and electronic properties. Here we report the synthesis of new type of photoluminescent silole. New siloles have been characterized by NMR, FTIR, and UV-vis absorption spectroscopy. Their optical characteristics have been also investigated using photoluminescence spectroscopy. Possible applications such as OLED and chemical sensors will be presented.