“…[1,4] Silicon based materials are widespread in use in photovoltaic devices, [5] molecular electronics, [6] and chemical and biological sensing, [7] and e. g. monolayers containing ferrocene units were intensively studied as electroactive molecules for charge storage. [8] Previously, we investigated azobenzene-modified monolayers on Si(111) for biosensor technology, [9] as well as two-state switching with thermally stable fulgimide monolayers, [10,11] and in the latter case a modulation between states with large nonlinear optical (NLO) contrast could be realized. [12] In this paper, we study 2H-naphtho [1,2-b]pyrans [13] 5, 12, 13, and especially the neat COOH-terminated monolayer on Si(111) containing compound 13 as headgroup (S6).…”