@misc{lindsey_taniguchi_balakumar_fan_2009, title={Methods and intermediates for the synthesis of porphyrins}, volume={7,582,751}, number={2009 Sep. 1}, author={Lindsey, J. S. and Taniguchi, M. and Balakumar, A. and Fan, D.}, year={2009} } @misc{balakumar_muthukumaran_lindsey_2009, title={Route to formyl-porphyrins}, volume={7,501,507}, number={2009 Mar 10}, author={Balakumar, A. and Muthukumaran, K. and Lindsey, J. S.}, year={2009} } @article{taniguchi_balakumar_fan_mcdowell_lindsey_2005, title={Imine-substituted dipyrromethanes in the synthesis of porphyrins bearing one or two meso substituents}, volume={9}, ISSN={["1099-1409"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-33244492173&partnerID=MN8TOARS}, DOI={10.1142/S1088424605000678}, abstractNote={ 5,15-substituted porphyrins are valuable compounds in bioorganic and materials chemistry. A new synthesis has been developed that employs 1,9-diformylation of a dipyrromethane, conversion of the diformyldipyrromethane to the bis(imino) derivative, and reaction of the bis(imino)dipyrromethane + a dipyrromethane to give the zinc-porphyrin bearing trans-AB-substituents. 1,9-diformylation was achieved via Vilsmeier reaction. Imination was achieved by treatment of the 1,9-diformyldipyrromethane with excess amine under neat conditions at room temperature. The porphyrin-forming reaction was carried out over 2 h in refluxing ethanol containing zinc acetate exposed to air. Oxidation of the intermediate porphyrinogen occurs aerobically. A complex composed of two bis(imino)dipyrromethanes and two zinc atoms was observed to form reversibly during the course of the reaction. A set of zinc-porphyrins with trans-AB-, A 2-, or A-substituents has been prepared in yields of ~30% (without detectable scrambling) with straightforward purification. The reaction is applicable to A/B substituent combinations of aryl/aryl, aryl/alkyl, and aryl/H. }, number={8}, journal={JOURNAL OF PORPHYRINS AND PHTHALOCYANINES}, publisher={World Scientific Pub Co Pte Lt}, author={Taniguchi, M and Balakumar, A and Fan, DZ and McDowell, BE and Lindsey, JS}, year={2005}, pages={554–574} } @article{balakumar_muthukumaran_lindsey_2004, title={A new route to meso-formyl porphyrins}, volume={69}, ISSN={["0022-3263"]}, DOI={10.1021/jo049819b}, abstractNote={Prior syntheses of porphyrins bearing meso-formyl groups have generally employed the Vilsmeier formylation of an acid-resistant copper or nickel porphyrin. A new approach for the synthesis of free base porphyrins bearing one or two (cis or trans) meso-formyl substituents entails the use of a dipyrromethane bearing an acetal group at the 5-position, a dipyrromethane-1-carbinol bearing an acetal group at the 5-position or carbinol position, or a dipyrromethane-1,9-dicarbinol bearing an acetal group at a carbinol position. Treatment of the resulting meso-acetal-substituted free base porphyrin to gentle acidic hydrolysis yields the corresponding meso-formyl porphyrin.}, number={15}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Balakumar, A and Muthukumaran, K and Lindsey, JS}, year={2004}, month={Jul}, pages={5112–5115} } @article{balakumar_lysenko_carcel_malinovskii_gryko_schweikart_loewe_yasseri_liu_bocian_et al._2004, title={Diverse redox-active molecules bearing O-, S-, or Se-terminated tethers for attachment to silicon in studies of molecular information storage}, volume={69}, ISSN={["1520-6904"]}, DOI={10.1021/jo034944t}, abstractNote={A molecular approach to information storage employs redox-active molecules tethered to an electroactive surface. Attachment of the molecules to electroactive surfaces requires control over the nature of the tether (linker and surface attachment group). We have synthesized a collection of redox-active molecules bearing different linkers and surface anchor groups in free or protected form (hydroxy, mercapto, S-acetylthio, and Se-acetylseleno) for attachment to surfaces such as silicon, germanium, and gold. The molecules exhibit a number of cationic oxidation states, including one (ferrocene), two [zinc(II)porphyrin], three [cobalt(II)porphyrin], or four (lanthanide triple-decker sandwich compound). Electrochemical studies of monolayers of a variety of the redox-active molecules attached to Si(100) electrodes indicate that molecules exhibit a regular mode of attachment (via a Si-X bond, X = O, S, or Se), relatively homogeneous surface organization, and robust reversible electrochemical behavior. The acetyl protecting group undergoes cleavage during the surface deposition process, enabling attachment to silicon via thio or seleno groups without handling free thiols or selenols.}, number={5}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Balakumar, A and Lysenko, AB and Carcel, C and Malinovskii, VL and Gryko, DT and Schweikart, KH and Loewe, RS and Yasseri, AA and Liu, ZM and Bocian, DF and et al.}, year={2004}, month={Mar}, pages={1435–1443} } @article{sazanovich_balakumar_muthukumaran_hindin_kirmaier_diers_lindsey_bocian_holten_2003, title={Excited-state energy-transfer dynamics of self-assembled imine-linked porphyrin dyads}, volume={42}, ISSN={["1520-510X"]}, DOI={10.1021/ic034558u}, abstractNote={Toward the development of new strategies for the synthesis of multiporphyrin arrays, we have prepared and characterized (electrochemistry and static/time-resolved optical spectroscopy) a series of dyads composed of a zinc porphyrin and a free base porphyrin joined via imine-based linkers. One dyad contains two zinc porphyrins. Imine formation occurs under gentle conditions without alteration of the porphyrin metalation state. Five imine linkers were investigated by combination of formyl, benzaldehyde, and salicylaldehyde groups with aniline and benzoic hydrazide groups. The imine-linked dyads are quite stable to routine handling. The excited-state energy-transfer rate from zinc to free base porphyrin ranges from (70 ps)(-)(1) to (13 ps)(-)(1) in toluene at room temperature depending on the linker employed. The energy-transfer yield is generally very high (>97%), with low yields of deleterious hole/electron transfer. Collectively, this work provides the foundation for the design of multiporphyrin arrays that self-assemble via stable imine linkages, have predictable electronic properties, and have comparable or even enhanced energy-transfer characteristics relative to those of other types of covalently linked systems.}, number={21}, journal={INORGANIC CHEMISTRY}, author={Sazanovich, IV and Balakumar, A and Muthukumaran, K and Hindin, E and Kirmaier, C and Diers, JR and Lindsey, JS and Bocian, DF and Holten, D}, year={2003}, month={Oct}, pages={6616–6628} }