This is a theoretical chemistry study to design singlet fission chromophores. Quantum chemistry methods MRSF-TDDFT and NEVPT2 are used to design chromophores with the building blocks of cyclic (alkyl)(amino)carbenes (CAACs). CAAC dimers with C2, C4 and p-phenylene spacers are considered. The substitutions with trifluoromethyls and fluorine atoms at the α position are investigated. The electronegative substituents enhance the π accepting capability of the α C, while maintaining it as a quaternary C atom. The phenylene-connected dimers with the two substitutions are identified as promising candidates for the singlet fission chromophores. The cylindrically symmetric C2 and C4 spacers allow for substantial structural reorganizations in the S0-to-S1 and S0-to-T1 excitations. Although the two substituted dimers with the C4 spacer satisfy (or very close to satisfy) the primary thermodynamics criterion for the singlet fission, the significant structural reorganizations result in high barriers so that the fission is kinetically unfavorable.