In the late 14th century, the Patriarchal Monastery of the Holy Trinity was one of the major hubs of the Tarnovo Literary School, which produced masterpieces such as the Tetraevangelia of Ivan Alexander and the Tomić Psalter. However, the Fall of Tarnovo to the Ottomans on 17 July 1393 meant an end to the monastery's heyday, and by 1416 the Bulgarian Patriarchate had been subordinated to the Patriarchate of Constantinople. Despite being arsoned, it nevertheless continued to exist, and in the 18th and early 19th century it was regularly the subject of donations by the rulers of Wallachia and Moldavia, the Romanian principalities across the Danube. Charters by Ştefan Cantacuzino (1715), Grigore II Ghica (1748), Alexander Ypsilantis (1776) and Constantine Ypsilantis (1803) have been preserved, and there is direct evidence of donations by earlier voivodes like Matei Basarab.