@article{liu_ptaszek_mass_minkler_sommer_bhaumik_lindsey_2014, title={Regioselective beta-pyrrolic electrophilic substitution of hydrodipyrrin-dialkylboron complexes facilitates access to synthetic models for chlorophyll f}, volume={38}, number={4}, journal={New Journal of Chemistry}, author={Liu, M. R. and Ptaszek, M. and Mass, O. and Minkler, D. F. and Sommer, R. D. and Bhaumik, J. and Lindsey, J. S.}, year={2014}, pages={1717–1730} }
 @article{mroz_bhaumik_dogutan_aly_kamal_khalid_kee_bocian_holten_lindsey_et al._2009, title={Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: Role of molecular charge, central metal and hydroxyl radical production}, volume={282}, ISSN={["1872-7980"]}, DOI={10.1016/j.canlet.2009.02.054}, abstractNote={The in vitro photodynamic therapy activity of four imidazole-substituted metalloporphyrins has been studied using human (HeLa) and mouse (CT26) cancer cell lines: an anionic Zn porphyrin and a homologous series of three cationic Zn, Pd or InCl porphyrins. A dramatic difference in phototoxicity was found: Pd cationic>InCl cationic>Zn cationic>Zn anionic. HeLa cells were more susceptible than CT26 cells. Induction of apoptosis was demonstrated using a fluorescent caspase assay. The anionic Zn porphyrin localized in lysosomes while the cationic Zn porphyrin localized in lysosomes and mitochondria, as assessed by fluorescence microscopy. Studies using fluorescent probes suggested that the cationic Pd porphyrin produced more hydroxyl radicals as the reactive oxygen species. Thus, the cationic Pd porphyrin has high potential as a photosensitizer and gives insights into characteristics for improved molecular designs.}, number={1}, journal={CANCER LETTERS}, author={Mroz, Pawel and Bhaumik, Jayeeta and Dogutan, Dilek K. and Aly, Zarmeneh and Kamal, Zahra and Khalid, Laiqua and Kee, Hooi Ling and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S. and et al.}, year={2009}, month={Sep}, pages={63–76} }
 @article{kee_bhaumik_diers_mroz_hamblin_bocian_lindsey_holten_2008, title={Photophysical characterization of imidazolium-substituted Pd(II), In(III), and Zn(II) porphyrins as photosensitizers for photodynamic therapy}, volume={200}, ISSN={["1873-2666"]}, DOI={10.1016/j.jphotochem.2008.08.006}, abstractNote={The photophysical properties of four imidazolium-substituted metalloporphyrins have been assessed to gain insights into the relative efficacy of the compounds for photodynamic therapy (PDT). A set of zinc(II), palladium(II), and chloro-indium(III) porphyrins all bear a net positive charge owing to the diethylimidazolium unit; one zinc chelate bears a negative charge owing to a bis(sulfobutyl)imidazolium unit. The photophysical properties of the cationic and anionic zinc porphyrins are very similar to one another in organic solvents, phosphate-buffered saline, and in the presence of bovine serum albumin. The properties of the zinc and palladium porphyrins bearing charged peripheral groups are generally similar to those of neutral analogs in organic solvents. The palladium porphyrin shows an essentially quantitative yield (≥0.99) of the triplet excited state compared to the zinc porphyrins (∼0.9), and all are quantitatively quenched (at the diffusion limit) by molecular oxygen in air-saturated fluid solution. If the rate constant and yield of quenching of the triplet excited state by energy or electron transfer to molecular oxygen is the same in the cellular environment as in solution, then these processes combined with the triplet yield contribute only a factor of 1.3 to the higher PDT activity of analogous palladium versus zinc porphyrins, which is much smaller than what is observed. Therefore, other factors such as transient reduction of the excited porphyrin or delivery to the target site must predominantly underlie the difference in PDT efficacy of these sensitizers.}, number={2-3}, journal={JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY}, author={Kee, Hooi Ling and Bhaumik, Jayeeta and Diers, James R. and Mroz, Pawel and Hamblin, Michael R. and Bocian, David F. and Lindsey, Jonathan S. and Holten, Dewey}, year={2008}, month={Dec}, pages={346–355} }
 @article{muthiah_bhaumik_lindsey_2007, title={Rational routes to formyl-substituted chlorins}, volume={72}, ISSN={["0022-3263"]}, DOI={10.1021/jo0707885}, abstractNote={Two distinct approaches have been developed for the synthesis of chlorins bearing formyl groups: (1) reaction of an acetal-substituted 1-acyldipyrromethane with 2,3,5,6-tetrahydro-1,3,3-trimethyldipyrrin to give upon hydrolysis a 5-formylchlorin and (2) Pd-mediated coupling of a bromochlorin with a one-carbon synthon (hydroxymethyl tributyltin or CO) to give a 13-, 15-, or 3,13-formylchlorin. The zinc chlorins exhibit long-wavelength peak absorption maxima ranging from 626 to 667 nm, indicating the wavelength tunability afforded by formyl substitution.}, number={15}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Muthiah, Chinnasamy and Bhaumik, Jayeeta and Lindsey, Jonathan S.}, year={2007}, month={Jul}, pages={5839–5842} }
 @article{yao_bhaumik_dhanalekshmi_ptaszek_rodriguez_lindsey_2007, title={Synthesis of porphyrins bearing 1-4 hydroxymethyl groups and other one-carbon oxygenic substituents in distinct patterns}, volume={63}, ISSN={["0040-4020"]}, DOI={10.1016/j.tet.2007.07.108}, abstractNote={Porphyrins that bear one-carbon oxygenic substituents (hydroxymethyl, formyl, ester) directly attached to the macrocycle afford a compact architecture of utility for diverse applications. Routes to 9 porphyrins bearing such groups in distinct architectures (A4-, trans-A2-, trans-A2B2-, trans-AB-, and trans-AB2C-porphyrins) have been explored (A=hydroxymethyl), including porphyrins bearing two one-carbon units in different oxidation states (hydroxymethyl/ester, formyl/ester). The hydroxymethyl group was introduced via TBDMS-protected dipyrromethane precursors.}, number={43}, journal={TETRAHEDRON}, author={Yao, Zhen and Bhaumik, Jayeeta and Dhanalekshmi, Savithri and Ptaszek, Marcin and Rodriguez, Phillip A. and Lindsey, Jonathan S.}, year={2007}, month={Oct}, pages={10657–10670} }
 @article{bhaumik_yao_borbas_taniguchi_lindsey_2006, title={Masked imidazolyl-dipyrromethanes in the synthesis of imidazole-substituted porphyrins}, volume={71}, ISSN={["0022-3263"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-33750879603&partnerID=MN8TOARS}, DOI={10.1021/jo061461r}, abstractNote={Imidazole-substituted metalloporphyrins are valuable for studies of self-assembly and for applications where water solubility is required. Rational syntheses of porphyrins bearing one or two imidazol-2-yl or imidazol-4-yl groups at the meso positions have been developed. The syntheses employ dipyrromethanes, 1-acyldipyrromethanes, and 1,9-diacyldipyrromethanes bearing an imidazole group at the 5-position. The polar, reactive imidazole unit was successfully masked by use of (1) the 2-(trimethylsilyl)ethoxymethyl (SEM) group at the imidazole pyrrolic nitrogen, and (2) a dialkylboron motif bound to the pyrrole of the dipyrromethane and coordinated to the imidazole imino nitrogen. The nonpolar nature of such doubly masked imidazolyl-dipyrromethanes facilitated handling. Selected masked dipyrromethanes were characterized by 11B and 15N NMR spectroscopy. Five distinct methods were examined to obtain trans-A2B2-, trans-AB2C-, and trans-AB-porphyrins. Each porphyrin contained one or two SEM-protected imidazole units. The SEM group could be removed with TBAF or HCl. Two zinc(II) porphyrins and a palladium(II) porphyrin bearing a single imidazole moiety were prepared and subjected to alkylation (with ethyl iodide, 1,3-propane sultone, or 1,4-butane sultone) to give water-soluble imidazolium- porphyrins. This work establishes the foundation for the rational synthesis of a variety of porphyrins containing imidazole units.}, number={23}, journal={JOURNAL OF ORGANIC CHEMISTRY}, publisher={American Chemical Society (ACS)}, author={Bhaumik, Jayeeta and Yao, Zhen and Borbas, K. Eszter and Taniguchi, Masahiko and Lindsey, Jonathan S.}, year={2006}, month={Nov}, pages={8807–8817} }
 @article{ptaszek_bhaumik_kim_taniguchi_lindsey_2005, title={Refined synthesis of 2,3,4,5-tetrahydro-1,3,3-trimethyidipyrrin, a deceptively simple precursor to hydroporphyrins}, volume={9}, ISSN={["1520-586X"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-26444474619&partnerID=MN8TOARS}, DOI={10.1021/op050087e}, abstractNote={2,3,4,5-Tetrahydro-1,3,3-trimethyldipyrrin (1) is a crucial building block in the rational synthesis of chlorins and oxochlorins. The prior 5-step synthesis of 1 from pyrrole-2-carboxaldehyde (2) employed relatively simple and well-known reactions yet suffered from several drawbacks, including limited scale (>/= 0.5 g of 1 per run). A streamlined preparation of 1 has been developed that entails four steps: (i) nitro-aldol condensation of 2 and nitromethane under neat conditions to give 2-(2-nitrovinyl)pyrrole (3), (ii) reduction of 3 with NaBH(4) to give 2-(2-nitroethyl)pyrrole (4), (iii) Michael addition of 4 with mesityl oxide under neat conditions or at high concentration to give gamma-nitrohexanonepyrrole 5, and (iv) reductive cyclization of 5 with zinc/ammonium formate to give 1. Several multistep transformations have been established, including the direct conversion of 2 --> 1. The advantages of the new procedures include (1) fewer steps, (2) avoidance of several problematic reagents, (3) diminished consumption of solvents and reagents, (4) lessened reliance on chromatography, and (5) scalability. The new procedures facilitate the preparation of 1 at the multigram scale.}, number={5}, journal={ORGANIC PROCESS RESEARCH & DEVELOPMENT}, publisher={American Chemical Society (ACS)}, author={Ptaszek, M and Bhaumik, J and Kim, HJ and Taniguchi, M and Lindsey, JS}, year={2005}, pages={651–659} }