Enantiopure distorted ribbon-shaped nanographene combining two-photon absorption-based upconversion and circularly polarized luminescence

Cruz, M. C., Marquez, I. R., Mariz, I. F. A., Blanco, V., Sánchez Sánchez, C., Sobrado, J. M., Martín Gago, J. A., Cuerva, J. M., Macoas, E., Campana, A. G. 2018. Enantiopure distorted ribbon-shaped nanographene combining two-photon absorption-based upconversion and circularly polarized luminescence. Chemical Science 9, 16, 3917-3924 DOI: 10.1039/c8sc00427g

Herein we describe a distorted ribbon-shaped nanographene exhibiting unprecedented combination of optical properties in graphene-related materials, namely upconversion based on two-photon absorption (TPA-UC) together with circularly polarized luminescence (CPL). The compound is a graphene molecule of ca. 2 nm length and 1 nm width with edge defects that promote the distortion of the otherwise planar lattice. The edge defects are an aromatic saddle-shaped ketone unit and a [5]carbohelicene moiety. This system is shown to combine two-photon absorption and circularly polarized luminescence and a remarkably long emission lifetime of 21.5 ns. The [5]helicene is responsible for the chiroptical activity while the push-pull geometry and the extended network of sp(2) carbons are factors favoring the nonlinear absorption. Electronic structure theoretical calculations support the interpretation of the results.

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