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Publications

(52) Ogata, F.; Nagaya, T.; Maruoka, Y.; Akhigbe, J.; Meares, A.; Lucero, M.; Satraitis, A.; Fujimura, D.; Okada, R.; Inagaki, F.; Choyke, P.; Ptaszek, M.; Kobayashi, H. Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer. Bioconjugate Chem. 2018, accepted for publication.

(51) Tivari, V.; Matutes, Y. A.; Konar, A.; Yu, Z.; Ptaszek, M.; Bocian, D. F.; Holten, D.; Kirmaier, C.; Ogilvie, J. P. Strongly Coupled Bacteriochlorin Dyad Studied Using Phase-Modulated Fluorescence-Detected Two-Dimensional Electronic Spectroscopy. Opt. Express, 2018, 26, 22327-22341.

(50) Meares, A.; Bhagavathy, G. V.; Zik, S. R.; Gallagher, T. Expanding p-Conjugation in Chlorins Using Ethenyl Linker. J. Org. Chem. 2018, 83, 9076-9087.

(49) McLeese, C.;. Yu, Z.; Esemoto. N. N.; Kolodziej, C.; Maiti, B.; Bhandari, Dunietz, B. D.; Burda, C.; Ptaszek, M. Excitonis Interactions in Bacteriochlorin Homo-Dyads Enable Ultrafast Charge Transfer: A Novel Approach to the Artificial Photosynthetic Special Pair. J. Phys. Chem. B, 2018, 122, 4131-4140.

(48) Esemoto, N. N.; Satraitis, A.; Wiratan, L.; Ptaszek, M. Symmetrical and Nonsymmetrical Meso–Meso Directly Linked Hydroporphyrin Dyads: Synthesis and Photochemical Properties. Inorg. Chem. 2018, 57, 2977-2988.

(47) Meares, A.; Satraitis, A.; Ptaszek, M. BODIPY–Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands. J. Org. Chem. 2017, 82, 13068-13075.

(46) Meares, A.; Satraitis, A.; Akhigbe, J.; Santhanam, N.; Swaminathan, S.; Ehudin, M.; Ptaszek, M. Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles. J. Org. Chem. 2017, 82, 6054-6070.

(45) Nopondo, E. N.; Yu, Z.; Wiratan, L.; Satraitis, A.; Ptaszek M.; Bacteriochlorin Dyads as Solvent Polarity Dependent Near-Infrared Fluorophores and Reactive Oxygen Species Photosensitizers. Org. Lett. 2016, 18, 4590-4593.

(44) Kang, H. S.; Esemoto, N. N.; Diers, J.; Niedzwiedzki, D.; Greco, J.; Akhigbe, J.; Yu, Z.; Pancholi, C.; Viswanathan B., G.; Nguyen, J. K.; Kirmaier, C.; Birge, R.; Ptaszek, M.; Holten, D.; Bocian, D. F. Effects of Strong Electronic Coupling in Chlorin and Bacteriochlorin Dyads J. Phys. Chem. A 2016, 120, 379-385.

(43) Meares, A.; Santhaman, N.; Satraitis, A. Yu, Z.; Ptaszek, M. Deep-red emissive BODIPY-chlorin arrays, excitable with green and deep-red light. J. Org. Chem. 2015, 80, 3858-3869.

(42) Faries, K.; M.; Diers, J. R.; Springer, J. W.; Yang, E.; Ptaszek, M.; Lahaye, D.; Krayer, M.; Taniguchi, M.; Kirmaier, C.; Lindsey, J. S.; Bocian, D. F.; Holten, D. Photophysical Properties and Electronic Structure of Chlorin-Imides: Bridging the Gap between Chlorins and Bacteriochlorins. J. Phys. Chem. B 2015, 119, 7503-7515.

(41) Ra, D.; Gauger, K. A.; Muthukumaran, K. ; Balasubramanian, B.; Chandrashaker, V.; Taniguchi, M.; Yu, Z.; Talley, D. C.; Ehudin, M.; Ptaszek, M.; Lindsey, J. S. Progress Towards Synthetic Chlorins with Graded Polarity, Conjugatable Substituents, and Wavelength Tunability. J. Porphyrins. Phthalocyanines. 2015, 19, 547-572.

(40) Yu, Z.; Pancholi, C.; Bhagavathy, G. V.; Kang, H, S.; Nguyen, J. K., Ptaszek, M. Strongly Conjugated Hydroporphyrin Dyads: Extensive Modification of Hydroporphyrins’ Properties by Expanding the Conjugated System J. Org. Chem. 2014, 79, 7910-7925.

(39) Harada, T.; Sano, K.; Sato, K.; Watanabe, R.; Yu, Z.; Hanaoka, H. Nakajima, T.; Choyke, P. L.; Ptaszek, M.; Kabayashi, H. Activatable Organic near-Infrared Fluorescent Probes Based on a Bacteriochlorin Platform: Synthesis and Multicolor in Vivo Imaging with a Single Excitation. Bioconjugate Chem. 2014, 25, 362-369.

(38) Liu, M.; Ptaszek, M.; Mass, O.; Minkler, D. F.; Sommer, R. D.; Bhaumik, J. Lindsey, J. S. Regioselective β-Pyrrolic Electrophilic Substitution of Hydrodipyrrin–Dialkylboron Complexes Facilitates Access to Synthetic Models for Chlorophyll f. New. J. Chem. 2014, 38, 1717-1730.

(37) Yu, Z.; Ptaszek, M. “Near-IR Emissive Chlorin-Bacteriochlorin Energy-Transfer Dyads with a Common Donor and Acceptors with Tunable Emission Wavelength.” J. Org. Chem. 2013, 78, 10678-10691.

(36) Chandrashaker, V.; Taniguchi, M.; Ptaszek, M.; Lindsey, J. S. “Competing Knorr and Fischer-Fink pathways to pyrroles in neutral aqueous solution.” Tetrahedron, 2012, 68, 6957-6967.

(35) Vinita, A. M.; Sano, K.; Yu, Z.; Nakajima, T.; Choyke, P.; Ptaszek, M.; Kobayashi, H. “Galactosyl human serum albumin-NMP1 conjugate: A near infrared-near (NIR)-activatable fluorescence imaging agent to detect peritoneal ovarian cancer metastases.” Bioconjugate Chem. 2012, 23, 1671-1679.

(34) Yu, Z.; Ptaszek, M. “Multifunctional Bacteriochlorins from selective palladium-coupling reactions.” Org. Lett. 2012, 14, 3708-3711.

(33) Mass, O.; Pandithavidana, D. R.; Ptaszek, M.; Santiago, K.; Springer, J. W.; Jiao, J.; Tang, Q.; Kirmaier, C.; Bocian, D. F.; Holten, D.; Lindsey, J. S. “De novo Synthesis and Properties of analogoues of the self-assembling Chlorosomal Bacteriochlorophylls.” New. J. Chem. 2011, 35, 2671-2690.

(32) Mass, O.; Taniguchi, M., Ptaszek, M., Springer, J. W., Faries, K. M., Diers, J. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S. “Structural characteristics that make chlorophylls green: interplay of hydrocarbon skeleton and substituents.” New J. Chem. 2011, 35, 76-88.

(31) Lindsey, J. S.; Chandrashaker, V.; Taniguchi, M.; Ptaszek, M. “Abiotic formation of uroporphyrinogen from acyclic reactants.” New J. Chem. 2011, 35, 65-75.

(30) Ptaszek, M.; Lahaye, D.; Krayer, M.; Muthiah C.; Lindsey, J. S. “De Novo Synthesis of Long-Wavelength Absorbing Chlorin-13,15-dicarboximides.” J. Org. Chem. 2010, 75, 1659-1673.

(29) Krayer, M.; Ptaszek, M.; Kim, H.-J.; Meneely, K. R.; Fan, D.; Secor K.; Lindsey, J. S. “Expanded Scope of Synthetic Bacteriochlorins via Improved Acid Catalysis Conditions and Diverse Dihydrodipyrrin-Acetals.” J. Org. Chem. 2010, 75, 1016-1039.

(28) Lindsey, J. S.; Ptaszek, M.; Taniguchi, M. “Simple Formation of an Abiotic Porphyrinogen in Aqueous Solution.” Origin of Life and Evolution of Biospheres. 2009, 495-515.

(27) Krayer, M.; Balasubramanian, T.; Ruzie, C.; Ptaszek, M.; Cramer, D. L.; Taniguchi, M.; Lindsey, J. S. Refined syntheses of hydrodipyrrin precursors to chlorin and bacteriochlorin building blocks. J. Porphyrins Phthalocyanines. 2009, 13, 1098-1100.

(26) Mass, O.; Ptaszek, M.; Taniguchi, M.; Diers, J. R.; Kee, H. L.; Bocian, D. F.; Holten, D.; Lindsey, J. S. Spectroscopic Properties of 12-Substituted versus 13-Substituted Chlorins. J. Org. Chem. 2009, 74, 5276-5289.

(25) Kee, H, L.; Diers, J. R.; Ptaszek, M.; Muthiah, C.; Fan, D.; Lindsey, J. S.; Bocian, D. F.; Holten D. Chlorin–Bacteriochlorin Energy-transfer Dyads as Prototypes for Near-infrared Molecular Imaging Probes: Controlling Charge-transfer and Fluorescence Properties in Polar Media. Photochem. Photobiol. 2009, 85, 909-920.

(24) Muthiah, C.; Lahayeé, D.;Taniguchi, M.; Ptaszek, M.; Lindsey, J. S. Regioselective Bromination Tactics in the De Novo Synthesis of Chlorophyll b Analogues. J. Org. Chem. 2009, 74, 3237-3247.

(23) Kee, H. L.; Nothdurft, R.; Muthiah, C.; Diers, J. R.; Fan, D.; Ptaszek, M.; Bocian, D. F.; Lindsey, J. S.; Culver, J. P.; Holten, D. Examination of chlorin-bacteriochlorin energy transfer dyads as prototypes for near-infrared molecular imaging probes. Photochem. Photobiol. 2008, 84, 1061-1072.

(22) Dogutan, D. K.; Ptaszek, M.; Lindsey, J. S. Rational or statistical routes from 1-acyldipyrromethanes to meso-substituted porphyrins. Distinct patterns, multiple pyridyl substituents, and amphipathic architectures.   J. Org. Chem. 2008, 73, 6187-6201.

(21) Muthiah, C.; Kee, H. L.; Diers, J. R.; Fan, D.; Ptaszek, M.; Bocian, D. F.; Holten, D.; Lindsey, J. S. Synthesis and excited-state photodynamics of a chlorin-bacteriochlorin dyad-through-space versus through-bond energy transfer in tetrapyrrole arrays. Photochem. Photobiol. 2008, 84, 786-801.

(20) Ptaszek, M.; Yao Z.; Savithri, D.; Boyle, P. D.; Lindsey, J. S. Synthesis and structural properties of simple porphyrin analogues of bacteriochlorophyll c. Tetrahedron 2007, 63, 12629-12638.

(19) Muthiah, C.; Ptaszek, M.; Nguyen, T.; Flack, K. M.; Lindsey, J. S. Two complementary routes to 7-substituted chlorins. Partial mimics of chlorophyll b. J. Org. Chem. 2007, 72, 7736-7749.

(18) Yao, Z.; Bhaumik, J.; Dhanalekshmi, S.; Ptaszek, M.; Rodriguez, Phillip, A.; Lindsey, J. S. Synthesis of porphyrins bearing 1-4 hydroxymethyl groups and other one-carbon oxygenic substituents in distinct patterns. Tetrahedron 2007, 63, 10657-10670.

(17) Kee, H. L.; Kirmaier, C.; Tang, Q.; Diers, J. R.; Muthiah, C.; Taniguchi, M.; Laha, J. K.; Ptaszek, M.; Lindsey, J. S.; Bocian, D. F.; Holten, D. Effects of substituents on synthetic analogs of chlorophylls. Part 2: Redox properties, optical spectra and electronic structure. Photochem. Photobiol. 2007, 83, 1125-1143.

(16) Kee, H. L.; Kirmaier, C.; Tang, Q.; Diers, J. R.; Muthiah, C.; Taniguchi, M.; Laha, J. K.; Ptaszek, M.; Lindsey, J. S.; Bocian, D. F.; Holten, D. Effect of substituents on synthetic analogues of chlorophylls. Part 1: synthesis, vibrational properties and excited-state decay characteristics. Photochem. Photobiol. 2007, 83, 1110-1124.

(15) Dogutan, D. K.; Ptaszek, M.; Lindsey, J. S. Direct synthesis of magnesium porphine via 1-formyldipyrromethane.   J. Org. Chem. 2007, 72, 5008-5011.

(14) Taniguchi, M.; Ptaszek, M.; McDowell, B. E.; Boyle, P. D.; Lindsey, J. S. Sparsely substituted chlorins as core constructs in chlorophyll analogue chemistry. Part 3: Spectral and structural properties.   Tetrahedron 2007, 63, 3850-3863.

(13) Taniguchi, M.; Ptaszek, M.; McDowell, B. E.; Lindsey, J. S. Sparsely substituted chlorins as core constructs in chlorophyll analogue chemistry. Part 2: Derivatization.   Tetrahedron 2007, 63, 3840-3849.

(12) Ptaszek, M.; McDowell, B. E.; Taniguchi, M.; Kim, H.-J.; Lindsey, J. S. Sparsely substituted chlorins as core constructs in chlorophyll analogue chemistry. Part 1: Synthesis.   Tetrahedron 2007, 63, 3826-3839.

(11) Kim, H.-J.; Dogutan, D. K.; Ptaszek, M.; Lindsey, J. S. Synthesis of hydrodipyrrins tailored for reactivity at the 1- and 9-positions.   Tetrahedron 2006, 63, 37-55.

(10) Laha, J. K.; Muthiah, C.; Taniguchi, M.; McDowell, B. E.; Ptaszek, M.; Lindsey, J. S. Synthetic Chlorins Bearing Auxochromes at the 3- and 13-Positions. J. Org. Chem. 2006, 71, 4092-4102.

(9) Ptaszek, M.; McDowell, B. E.; Lindsey, J. S. Synthesis of 1-formyldipyrromethanes.   J. Org. Chem. 2006, 71, 4328-4331.

(8) Rodakiewicz-Nowak, J.; Nowak, P.; Rutkowska-Zbik, D.; Ptaszek, M.; Michalski, O.; Mynarczuk, G.; Eilmes, J. Spectral and electrochemical characterization of dibenzotetraaza[14]annulenes.   Supramol. Chem. 2005, 17, 643-647.

(7)  Ptaszek, M.; Bhaumik, J.; Kim, H.-J.; Taniguchi, M.; Lindsey, J. S. Refined synthesis of 2,3,4,5-tetrahydro-1,3,3-trimethyldipyrrin, a deceptively simple precursor to hydroporphyrins.   Org. Proc. Res. Dev. 2005, 9, 651-659.

(6)  Muthukumaran, K.; Ptaszek, M; Noll, B.; Scheidt, W. R.; Lindsey, J. S. Boron-complexation strategy for use with 1-acyldipyrromethanes.   J. Org. Chem. 2004, 69, 5354-5364.

(5)  Eilmes, J.; Ptaszek,* M.; Dobrzycki, L.; Wozniak, K. New alkoxycarbonyl derivatives of dibenzotetraaza[14]annulene. Crystal and molecular structure of [5,14-dihydro-7,16-diisopropoxycarbonyl-8,15-dimethyl-6,17-diphenyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinato(2-)- 4N]nickel(II).   Polyhedron 2003, 22, 3299-3305.

(4) Eilmes, J.; Ptaszek, M.; Wozniak, K. Synthesis, reactivity, crystal and molecular structure of [5,14-dihydro-7,16-bis(2-oxo-3H-furan-5-yl)-6,8,15,17-tetramethyldibenzo[b,i][1,4,8,11]tetraazacyclotetradecinato(2-)- 4N]nickel(II).   Polyhedron 2002, 21, 7-17.

(3) Eilmes, J.; Ptaszek, M.; Zielinska, K. A new synthetic strategy towards dibenzotetraaza[14]annulenes bearing alkoxycarbonyl and aryloxycarbonyl pendant substituents.   Polyhedron 2001, 21, 143-149.

(2) Eilmes, J.; Ptaszek, M.; Dibenzotetraaza[14]annulenes, part II. Wiadomości Chemiczne, 1999, 53, 329-351.

(1) Eilmes, J.; Ptaszek, M. Dibenzotetraaza[14]annulenes. Part I.   Wiadomosci Chemiczne 1999, 53, 305-328.