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Optical properties of two series of fully conjugated cyclo[n]thiophenes were analyzed experimentally and theoretically. The absorption spectra reveal a shift to higher wavelengths with increasing size of the cycles, which can be successfully described by an excitonic approach based on a Frenkel exciton Hamiltonian. Furthermore, intriguing new bands in the absorption and fluorescence spectra of the smaller macrocycles disclose the dominance of their ring strain.