Electronic Absorption, Emission and Two-PhotonAbsorption Properties of Some Functional1,3,5-Triphenylbenzenes

We report herein the linear optical properties of some extended 1,3,5‐triphenylbenzene derivatives 1,3,5‐[(1, 4‐C6H4)C≡C(4‐C6H4X)]3(C6H3) (3‐X; X=NO2, CN, H, OMe, NMe2, NPh2) and briefly discuss the two‐photon absorption (2PA) cross‐sections determined for the derivatives featuring the most electron‐rich substituents, contrasting their 2PA performance with the 2PA values previously gathered for their triphenylisocyanurate analogues N,N’,N”‐[(1, 4‐C6H4)C≡C(4‐C6H4X)]3(N3{C(O)}3) (1‐X). When functionalized by electron‐releasing substituents at their periphery, 3‐X derivatives are potent substitutes for 1‐X compounds in NLO applications, especially when maximal transparency is not required in the visible range. Some rationalization of this unexpected outcome is proposed based on DFT calculations.The CNRS (PICS program N8 7106 and LIA N8 1194) and ANR (Isogate Project) are acknowledged for financial support. S.S is the recipient of an Australian Postgraduate Award and thanks the Rennes Metropole for a Mobility Grant, the Australian Nanotechnology Network for an Overseas Grant, and the ANU for travel support under the Higher Degree Research Students Travel Grant Scheme. F.P. and A.N.N. thank the Region Bretagne for a Ph.D. grant. Mireille Blanchard-Desce (UMR 5255, Bordeaux) is acknowledged for providing providing access to two-photon excited fluorescence facilities. M.G.H. thanks the Australian Research Council (ARC) for financial support. We also acknowledge the HPC resources of CINES and of IDRIS under the allocations 2016-2017[x2016080649] made by GENCI (Grand Equipement National de Calcul Intensif)