Fluorescent chemosensors on the basis of naphtho[1,8-bc]pyrans

Pyran derivatives peri-fused to acenaphthene and acenaphthylene

“…peri-Fused bis-pyran systems like 1,6-and 1,8-dioxapyrenes exhibited unusual photobiological and genotoxic activity [3,4], readily formed charge-transfer complexes [5], and were used as building blocks for the synthesis of so-called organic metals [6]. We previously synthesized 2-acylnaphtho[1,8-bc]pyran-3-ones and coordination compounds based thereon, which showed strong yellow-orange fluorescence and were proposed as effective chemosensors and highly sensitive analytical reagents for qualitative and quantitative determination of heavy metals [7]. Naphtho[1,8-bc]-pyran-3-ones were obtained by bromination of periacyloxynaphthyl alkyl ketones at the side alkyl chain OH Ac I OAc Ac II Ac 2 O, NaOAc OBz Ac III PhCOCl, pyridine OAc COCH 2 Br VI 1,4-Dioxane · Br 2 OH Ac IV CuBr 2 , EtOAc-CHCl 3 , Δ Br CuBr 2 , EtOAc-CHCl 3 , Δ OBz COCH 2 Br V Scheme 1.…”