Novel derivatives of 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic acid: synthesis, electrochemical and optical properties

Abstract

Facile synthesis and opto-electrochemical properties of various unsymmetrically “peri”-substituted perylene derivatives, with four chloro-atoms at the bay-positions, have been reported.

Perylenetetracarboxy-3,4:9,10-diimide derivatives with large two-photon absorption activity

“…52 For the derivatives substituted with 4-(R-ethynyl)phenoxy moieties we observe a blurring of the vibronic structure and a bathochromic shift of the lowest-energy intense band, at ca 570-590 nm ( Figure 2), as expected for the presence of tetraphenoxy bay-substituted compounds, because of the loss of rigidity due to core twisting and slight electron-donating nature of phenoxy substituents. 53,54 However, the peak position was almost the same for all substituents at bay position. In the case of P2, the absorption bands of the PTCDI core and the di(thienyl)benzothiadiazole moiety [55][56][57] are partially superimposed.…”

“…56 N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrachloro-3,4:9,10perylenetetracarboxydiimide (I1) was prepared as reported in Scheme 1 following a well-known synthetic procedure. 53,60,61 Synthesis of the alkyne D. First 4 mL); the reaction mixture was stirred at 0°C for 10 min and then at room temperature for 1 h; propargyl chloride (206 µL, 2.86 mmol) was added at 0°C and the mixture was stirred at room temperature overnight; the reaction mixture was quenched with water (50 mL) and extracted with ethylacetate (3x50mL); the organic layer was dried on Na 2 SO 4 and the solvent was removed at reduced pressure to give the crude product that was purified by flash chromatography using hexane/dichloromethane 1/1 as eluent; the pure product was obtained in 90% yield. 1 1,6,7,12-tetrakis(4-iodophenoxy)-N,N'-(2,6 1,6,7,12-Tetrakis[4-(phenylethynyl)phenoxy-N,N'-(2,6diisopropylphenyl)perylenetetracarboxy-3,4:9,10-diimide (P1) was prepared following the above reported general procedure using 160 L (d=0.95g/mL) of phenylacetylene (A), the eluent for flash chromatography being hexane/dichloromethane 1/1.…”

Overcoming the exciton binding energy in two-dimensional perovskite nanoplatelets by attachment of conjugated organic chromophores

“…Toluene was evaporated under vacuum and the solid residue was washed with water and methanol. Subsequently, the solid residue was dried and chromatographed on silica, with CH 2 Cl 2 to afford the desired product (0.52 g, 85%) 34 . 1 Supplementary Figs.…”

“…The PDI with the alkylammonium linker at the imide position and four chlorine atoms in the "bay-area" was synthesized in two steps from a perylene monoimide monoanhydride derivative as described in the methods section and Supplementary Figs. 3, 4 and 5 34 . The alkylammonium group is introduced so that it can coordinatively attach to the surface of the NPLs 30 , while the chlorine atoms ensure sufficient solubility in common organic solvents such as dichloromethane (DCM).…”

“…In this work, we explore the introduction of functional organic cations in 2D perovskites in order to enhance their functionality by, for example, inducing change separation from the inorganic octahedral layer into the organic chromophores. Specifically, we have replaced the non-functional organic ligands at the surface of colloidal NPLs by strong electron-accepting PDIs 34 . The NPLs are colloidal quasi-2D cesium lead bromide NPLs consisting of four layers of lead bromide octahedra (CsPbBr 3 NPLs, n = 4) [26][27][28] .…”