Solvent effects on 2,3-bis(chloromethyl)-1,4-anthraquinone (DCMAQ) and the molecular recognition of DCMAQ in calix[8]arene were investigated using optical absorption and fluorescence emission techniques. Optical absorption spectra show n-->pi(*) band in 350-500 nm region. It also indicates that the dipole-dipole interaction and solvent reorganization energies are responsible for the observed features in different solvents. The observed quantum yield of DCMAQ in different solvents is due to the formation of intermolecular hydrogen bond and reorientation of solvent molecule in the excited state of DCMAQ. Excited state dipole moment of DCMAQ is calculated by solvatochromic data and it shows a higher excited state dipole moment than ground state dipole moment. Optical absorption and fluorescence studies of DCMAQ in calix[8]arene elucidate the evidence for the formation of complex between DCMAQ and calix[8]arene. The inclusion ratios and inclusion constant of the host-guest complexes are also determined.