We describe the application of molecular modeling to study problems related to the packing and conformation of oligofluorene molecules in the solid state. First of all, we describe an improved force field for oligofluorenes. The model is based on the MM3 force field for the intramolecular degrees of freedom, but it relies oil A initio calculations for the torsion potential between two monomers and the electrostatic interactions. We also report ab initio calculations of the interaction potentials between fluorene and fluorenone units. The force field has been tested on the crystal structures of a fluorene monomer, a dimer, and a pentamer containing a fluorenone at the center. It has then been employed to Study conformational defects of the chains, both ill vacuo and in the bulk. We find that certain modes of inversion from right-handed to left-handed helices are also possible within the constraining environment of the crystals. The effect of the presence of two different types of side chains has been also addressed. Finally, the possibility of having two fluorene units parallel and close to each other has been investigated as a model of a ground-state precursor of an excimer. Our Simulations show that this configuration is sterically and energetically unfavorable so that formation of all excimer following optical excitation appears to be unlikely.