Advances made in methods of synthesis of siloles during the period 1996 to the end of 2009 are described. The earliest general method involved reductive dimerization of tolan with lithium metal followed by quenching with a dichlorosilane, trichlorosilane, or silicon tetrachloride. Versatile new methods involve the intramolecular cyclization of dialkynylsilanes in the presence of lithium naphthalenide (Tamao method) and 1,1-organoboration with a trialkylborane (Wrackmeyer method) each of which provides an entry into different types of substitution patterns in the silole product. Supplementing the reductive-coupling route to siloles has been both stoichiometric and catalyzed processes mediated by transition metal complexes. Various, less general synthetic methods are also described. Reactions of siloles at either the silicon center or the ring carbon centers that retain the silole skeleton are included. Characterization methods used to confirm the siloles are included in tabular form, and uses or applications of the silole are also summarized. Fluorescent data are highlighted for selected siloles as is the aggregation-induced emission phenomenon generally exhibited by this class of compounds. Various oligomers and polymers that contain siloles have been reported and include oligo- and poly-(1,1-siloles) as well as polymers where organic bridges connect to the silole in the 1-position or at a ring carbon position. Siloles have been used as core components for efficient electron-transporting materials and their incorporation into OLED devices and the characteristics of such devices is summarized.