Robust cation-radical salts derived form chiral organic electron donors hold potential to be utilized as chrioptical switches in the emerging area of molecular electronics and nanotechnology. It is noteworthy that 9,9-dialkyfluorenes has been extensively investigated as building blocks for the preparation of a variety of electro-active materials. Thus, we conjectured that a chiral analogue of 9,9-dialkyfluorene can serve as a precursor to a variety of chiral electro-active materials. According herein we will present the preparation of a variety of fluorene derivatives in which a chiral cholesterol group is attached to the carbon 9 of the fluorene moiety (see structure A below). Many of these chiral fluorene derivatives form stable cation-radical salts that can be readily isolated as robust hexachloroantimonate salts. Moreover, the simplest cholesterol-fluorene derivatives (i.e. R and R' = H) can also be converted into oligofluorenes in which the cholesterol moieties serve not only as groups that impart chirality into these oligomeric materials but also allows them to soluble in common organic solvents . The details of these works will be discussed in this poster.