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• 1066-54-2 trimethylsilylacetylene 
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• 262267-34-5 S-2-pyridyl 4-[2-(trimethylsilyl)ethynyl]benzothioate 
• 159152-14-4 5-(mesityl)dipyrromethane 
• 307930-98-9 1-(4-iodobenzoyl)-5-mesityl-9-{4-[2-(trimethylsilyl)ethynyl]benzoyl}dipyrromethane 

Relevant academic research and scientific papers

Porphyrins Bearing Arylphosphonic Acid Tethers for Attachment to Oxide Surfaces

Synthetic molecules bearing phosphonic acid groups can be readily attached to oxide surfaces. As part of a program in molecular-based information storage, we have developed routes for the synthesis of diverse porphyrinic compounds bearing phenylphosphonic acid tethers. The routes enable (1) incorporation of masked phosphonic acid groups in precursors for use in the rational synthesis of porphyrinic compounds and (2) derivatization of porphyrins with masked phosphonic acid groups. The precursors include dipyrromethanes, monoacyldipyrromethanes, and diacyldipyrromethanes. The tert-butyl group has been used to mask the dihydroxyphosphoryl substituent. The di-tertbutyloxyphosphoryl unit is stable to the range of conditions employed in syntheses of porphyrins and multiporphyrin arrays yet can be deprotected under mild conditions (TMS-C1/TEA or TMS-Br/TEA in refluxing CHCl3) that do not cause demetalation of zinc or magnesium porphyrins. The porphyrinic compounds that have been prepared include (1) A3B-, trans-AB 2C-, and ABCD-porphyrins that bear a single phenylphosphonic acid group, (2) a trans-A2B2-porphyrin bearing two phenylphosphonic acid groups, (3) a chlorin that bears a single phenylphosphonic acid group, and (4) a porphyrin dyad bearing a single phenylphosphonic acid group. For selected porphyrin-phosphonic acids, the electrochemical characteristics have been investigated for molecules tethered to SiO2 surfaces grown on doped Si. The voltammetric behavior indicates that the porphyrin-phosphonic acids form robust, electrically well-behaved monolayers on the oxide surface.

SYNTHESIS OF PERYLENE-PORPHYRIN BUILDING BLOCKS AND POLYMERS THEREOF FOR THE PRODUCTION OF LIGHT-HARVESTING ARRAYS

The present invention provides methods, compounds, and compositions for the synthesis of light harvesting arrays, such arrays comprising: (a) a first substrate comprising a first electrode; and (b) a layer of light harvesting rods electrically coupled to said first electrode, each of said light harvesting rods comprising a polymer of Formula (I): wherein m is at least 1; X1 is a charge separation group, and X2 through Xm+1 are chromophores. At least one of X2 through Xm+1 has at least one perylene group coupled thereto.

Design and synthesis of light-harvesting rods for intrinsic rectification of the migration of excited-state energy and ground-state holes

We present the design of molecular materials for ultimate use in solid-state solar cells. The molecular materials are semi-rigid oligomeric rods of defined length with metalloporphyrins in the backbone and a carboxy group at one end for attachment to a su

Rational syntheses of cyclic hexameric porphyrin arrays for studies of self-assembling light-harvesting systems

Two new cyclic hexameric arrays of porphyrins have been prepared in a rational, convergent manner. The porphyrins in each cyclic hexamer are joined by diphenylethyne linkers affording a wheel-like array with a diameter of ～35 A. One array is comprised of

Rational Syntheses of Porphyrins Bearing up to Four Different Meso Substituents

Porphyrins bearing specific patterns of substituents are crucial building blocks in biomimetic and materials chemistry. We have developed methodology that avoids statistical reactions, employs minimal chromatography, and affords up to gram quantities of regioisomerically pure porphyrins bearing predesignated patterns of up to four different meso substituents. The methodology is based upon the availability of multigram quantities of dipyrromethanes. A procedure for the diacylation of dipyrromethanes using EtMgBr and an acid chloride has been refined. A new procedure for the preparation of unsymmetrical diacyl dipyrromethanes has been developed that involves (1) monoacylation with EtMgBr and a pyridyl benzothioate followed by (2) introduction of the second acyl unit upon reaction with EtMgBr and an acid chloride. The scope of these acylation methods has been examined by preparing multigram quantities of diacyl dipyrromethanes bearing a variety of substituents. Reduction of the diacyl dipyrromethane to the corresponding dipyrromethane-dicarbinol is achieved with NaBH4 in methanolic THF. Porphyrin formation involves the acid-catalyzed condensation of a dipyrromethane-dicarbinol and a dipyrromethane followed by oxidation with DDQ. Optimal conditions for the condensation were identified after examining various reaction parameters (solvent, temperature, acid, concentration, time). The conditions identified (2.5 mM reactants in acetonitrile containing 30 mM TFA at room temperature for 3B, trans-A2B2, trans-AB2C, cis-A2B2, cis-A2BC, and ABCD were prepared, including >1-g quantities of three porphyrins.