Yamamoto or Suzuki-Miyaura coupling polymerizations of 2,3-diiodo-N-cyclohexylmaleimide with fluorene derivatives (2,7-dibromo-9,9-dihexylfluorene and 9,9-dihexylfluorene-2,7-diboronic acid) were carried out. The number-average molecular weights (M-n) of the resulting copolymers were 2600-3500 by gel permeation chromatography analysis. The fluorescence emission of the alternating copolymer showed the emission maxima at 551 nm in THF. On the other hand, the random copolymers showed the bimodal emission peaks at 418-420 and 555-557 nm region, respectively. The fluorescence peaks of the random copolymers on the long wavelength region (555-557 nm) were attributed to the conjugated neighboring N-cyclohexylmaleimide-9,9-dihexylfluorene units in the polymer main chain. Furthermore, the copolymers exhibited the fluorescence solvatochromism by the difference of the polarity of solvents. The alternating and random copolymers showed the different fluorescence solvatochromism, and the emission colors are distinguishable by the naked eye, respectively. (c) 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4945-4956