In this paper, we have designed a solution processable macroscopically oriented conductive polymer of fluorene dangled 3-pentadecylphenol (Polyfluorene pentadecyl benzene, PFLPDB) through side chain engineering and self-assembly approach. Initially fluorene was coupled with 3-pentadecylphenol (3-PDP) and further subjected to oxidative polymerisation in the presence of anhydrous ferric chloride (FeCl3). Effects of polarity of the solvent and time on self-assembly process was studied using various microscopic techniques which suggested the formation of macroscopically oriented fibers having 20–30 nanometer diameter in chloroform with an electrical conductivity of (2.1・10–2 S・cm–1). Optical and electrochemical band gaps were calculated from the studies made by UV-Vis spectroscopy and cyclic voltammetry. Its field effect transfer characteristics were further studied by fabricating an Organic field effect transistor (OFET) device having configuration (Si/SiO2/PFLPDB/Ag) and measured its field effect mobility (1.076 cm2・v–1・s–1) at 1 V and ON/OFF ratio of the device calculated as 1.82・103 suggests its application as an excellent active material for organic microelectronics.