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The earliest known works by Dionysius were the frescoes in the Nativity Cathedral of St Pafnuty’s Borovsky Monastery, executed jointly with the monastic elder Mitrofan between 1467 and 1476. This fact is recorded in the chronicles and the Life of St Pafnuty of Borovsk, who founded the Monastery. These murals no longer exist, since the Cathedral was demolished and rebuilt in the late 16th century.
In 1481 Dionysius headed a crew of painters who created the first iconostasis in the Assumption Cathedral in the Moscow Kremlin. Two biographic icons depicting St Pyotr and St Alexis, metropolitans of Moscow, may have been intended for the local tier of that iconostasis. In 1484, along with his sons Feodosy and Vladimir, the master began to paint the murals in the Assumption Cathedral of St Iosif’s Volokolamsky Monastery at the request of its founder, the Venerable Iosif Volotsky.
In the 1490s Dionysius and his colleagues apparently moved to the Beloozero region in the Russian North. His most famous masterpieces from that period are the icon "The Crucifixion" (1500) from St Pavel’s Obnorsky Monastery and the frescoes and iconostasis of The Nativity Cathedral of Virgin Mary, located in St Ferapont’s Monastery (1502). The art of Dionysius embodies the greatest Russian spiritual pursuits and artistic achievements of the late 15th and early 16th century. Clarity of composition, elongated proportions of figures and bright colouring dominated by pure, sonorous tones impart a special grace to the works of this master
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