Synthesis and photophysical studies of through-space conjugated [2.2]paracyclophane-based naphthalene fluorophores

In this work we report a straightforward method for the synthesis of a new class of small organic fluorophores bearing both [2.2]paracyclophane and naphthalene subunits using an intramolecular dehydrogenative Diels-Alder reaction as a key step. These compounds are characterized by a compact three-dimensional structure as well as through-space conjugated push-pull systems, and possess interesting spectroscopic characteristics that may be useful for the development of innovative chemical probes and optical sensors. New three-dimensional compact organic fluorophores with tunable photophysical properties are easily accessible from [2.2]paracyclophane using an intramolecular dehydrogenative Diels-Alder reaction as a key step.