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The monograph summarizes and analyzes all works, known to the authors, devoted to experimental and theoretical studies of electronic structure and spectral properties of numerous synthesized and modelled heterocirculenes, as well as the prospects of their further functionalization in one- and two-dimensional polymers by the example of tetraoxa[8]circulenes. Particular attention is paid to analysis of aromaticity of hetero[8]circulene molecules containing an antiaromatic inner core, whose planar structure is stabilized by an external polyaromatic system of arene and/or heteroarene rings. The high thermal and chemical stability of the most heterocirculenes in combination with semiconducting properties suggest that these compounds are promising materials for molecular electronics and nanophotonics. The monograph is intended for a wide range of specialists - organic chemists, physicists, chemists-analysts, spectroscopists and everybody who are interested in study of electronic structure and spectral properties of molecules.