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For the first time, four series of new phthalide-containing heteroaromatic compounds were separated by reverse phase HPLC OYO, OYS, SYS; OYOYO, OYOYS, SYOYS; SYSYS, SYSYO, OYSYO; OYYO, OYYS, SYYS, (where O - diphenyloxide, S - diphenylsulfide, Y - phthalide group). A fundamental difference was established in the chromatographic behavior of diaryl(arylene)diphthalides, built on the principle of "head-to-tail", and diaryldiphthalides with a structure of "head-to-head". The meso and chiral diastereoisomers of the former were eluted by one peak, while the latte