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A method for regioselective synthesis of 2,4-disubstituted and more highly substituted fluorenols using catalytic [2+2+2]cyclotrimerization of mono- and disubstituted diynes with terminal alkynes was explored. In the former case, the preferential formation of the 2,4-regioisomers was achieved in the presence of Cp*Ru(cod)Cl, whereas Rh-based catalysts tended to provide 3,4-regioisomers as the major products. The 2,4-disubstituted fluorenols were converted into the corresponding 9,9′-spirobifluorene derivatives and their structural and photophysical properties were evaluated.