Synthesis and Two‐Photon Properties of Multi‐Branched Fluorophores Composed of Ladder‐Type Conjugated Cores and Functionalized Diquinoxalinylamino Peripheries

Abstract

Two multipolar fluorophores using ladder‐type oligo‐(p‐phenylene) units as the central π‐bridges and functionalized diquinoxalinylamino moieties as the peripheral groups have been synthesized and experimentally shown to manifest strong two‐photon absorption (2PA) and medium‐high up‐converted emission properties in the near‐IR (NIR) spectral region under the irradiation of femtosecond laser pulses. Tentative analysis of the structure–2PA property revealed that in the presented structural combination, diquinoxalinylamino units are useful 2PA‐enhancing subunits when properly incorporated. The π‐conjugation length of the central oligo‐(p‐phenylene) components was also found to be one of the key parameters that relates to the magnitude of the overall molecular 2PA properties in the studied molecular system, and this structural motif provides access to highly efficient two‐photon absorbers with large two‐photon action cross‐section values.

Mechanochemical synthesis of biphenyl-derived organic fluorescent materials via solvent-free and ligand-free oxidative homocoupling reactions

“…The starting materials were obtained from commercial suppliers (Shanghai Accela ChemBio Co., Ltd, Shanghai Yien Chemical Technology Co., Ltd, and Shanghai Aladdin Biochemical Technology Co., Ltd) and used as received. N -phenyl- N -[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(1,2,2-triphenylethenyl)-benzenamine ( 1 ) 23 and 9,9-dihexyl-2-fluoreneboronic acid ( A2 ) 24 were synthesized according to literature procedures. The synthetic process of the new compound (4-(phenyl(4-(1,2,2-triphenylvinyl)phenyl)amino)phenyl)boronic acid ( A6 ) using intermediate 1 is shown in the ESI †.…”

Heavy atom enhanced generation of singlet oxygen in novel indenofluorene-based two-photon absorbing chromophores for photodynamic therapy

“…Ladder-type oligo-p-phenylenes are good building blocks to construct materials with large TPA cross-section values owning to their planar chemical structures with extended p-conjugation [21,22]. In our previous reports, the relationship between TPA properties of ladder-type oligo-p-phenylene-cored chromophores and their conjugation lengths was systematically investigated [23,24].…”

Synthesis and Ultrafast Broadband Optical Limiting Properties of a Two-Branched Twistacene

“…Together with a broadband excited state absorption (ESA), OL performance will be significantly improved under the various wavelengths, which is a key factor to realize the broadband response to different input laser wavelengths. In addition, the zero contribution of one photon absorption in this process will provide a high optical transparency, avoiding the loss of light under low laser beam intensity caused by linear absorption [ 13 , 14 , 15 , 16 ]; however. constructing these materials remains a challenge.…”