Preparation and Synthetic Applications of Phototropone

Abstract

An optimized multigram-scale route to phototropone (bicyclo[3.2.0]­hepta-2,6-dien-7-one) is reported via the 4-π-photocyclization of tropone complexed to Lewis acid. Phototropone is a highly versatile molecular building block, and its conversion into 18 novel derivatives using standard transformations is demonstrated, allowing access to a variety of rigid bicyclic scaffolds.

A Predictive Screening Tool to Evaluate the Efficiency of Z/E Photoisomerizable Molecular Switches

“…Numerous families of light-driven molecular switches are known and their performance has been studied, [13][14][15] based on different photoreactivities coupled to a vast variety of physicochemical properties and photo-modulable applications. [16][17][18] Among them, light-induced cyclization and Z/E isomerization are possibly the most applied photoswitching reactions: on one hand, photocyclization was invoked to obtain versatile molecular building blocks, [19][20][21] to propose various molecular solar thermal systems (MOST), [22][23][24][25][26][27][28] and to develop different generations of donor-acceptor Stenhouse adducts (DASA). [29][30][31][32][33][34][35][36] On the other hand, Z/E photoisomerization has been inspired by different sources: 16 biological chromophores, such as the retinal chromophore in rhodopsins [37][38][39][40][41] or the green fluorescent protein (GFP) chromophore, [42][43][44] but also artificial prototypes, such as the family of chiroptical switches designed by the group of Feringa, [45][46][47] stilbene-based [48][49][50] or hemithioindigo-based [51][52]…”