Tripodal pyrene chromophores for semiconductor sensitization: new footprint design

Modular synthesis of ruthenium tripodal system with variable anchoring groups positions for semiconductor sensitization

“…Based on the synthesis described in this paper and our previous work 5 we conclude that a good strategy, summarized in Scheme 1, is to add the chromophore (or ligand) first, when the chromophore (or ligand) is polar, and to add the anchor unit first, when the chromophore is non polar (for instance, 1-ethynyl-pyrene). 5 The separation by silica gel column chromatography of polar products formed in the statistical step was easier. Low conversions were preferred, because the formation of tri-and tetra-substituted products is avoided, and any unreacted starting material can be recycled.…”

“…The following compounds were prepared according to published literature procedures: 1,3,5,7-tetrakis(4-iodophenyl)adamantane, 8 methyl 4-ethynylbenzoate, 9 and methyl 3-ethynylbenzoate. 5,9 Melting points are uncorrected. 1 H NMR and 13 C NMR spectra were acquired on a Varian INOVA 500 spectrometer operating at 499.896 MHz for 1 H, and 125.711 MHz for 13 C at room temperature in CDCl 3 , THF-d 8 or acetone-d 6 as noted.…”

“…More recently, we studied dyedye interactions on the surface of semiconductor nanoparticles and other surfaces using large footprint tripods capped with pyrene. 5,6 This kind of molecule-tripodal linker models are also finding application as novel photochromic materials, 4a and for the chemical modification of probes used for atomic force microscopy (AFM). 3d,4d In general, the synthesis and purification of tripodal compounds are lengthy, proceed in low-yields, and it is difficult to vary the footprint sizes or the anchoring groups.…”

Synthesis and Structural Analysis of Substituted Tripod‐Shaped Tri‐ and Tetra(p‐phenylene)s

“…(i) "molecular caltrops" with four phenylacetylene legs extending from either a tetrahedral silicon core [6,7] or from an adamantane core, [8,9] (ii) conically shaped dendron adsorbates with a functional group at the core, [10][11][12][13] and (iii) tripod-shaped oligo(p-phenylene)s joined together by a single silicon atom [14,15] to be used for the functionalization of different surfaces ( Figure 1). However, these reported tripodshaped molecules cannot be used for biological applications, because the hydrophobic tripod framework, or in some cases its alkyl side chains, [14] are known to interact nonspecifically with protein molecules, thus interfering with the specific interaction of target molecules with the ligand on the focal point of the tripod.…”

Synthesis of an azobenzene-linker-conjugate with tetrahedrical shape

“…[6][7][8] Moreover, p-aggregation of the attached chromophores is a known problem that changes or even suppresses the chromophore properties. 6,9 Recently, Galoppini,9,12 Tour, 10,11 and others. [13][14][15][16][17] have developed three-dimensional linkers with a tetrahedrical core unit for sufficient control of the perpendicular shape and the headgroup to surface distance.…”