@article{kodali_mancini_solomon_episova_roach_hobbs_wagner_mass_aravindu_barnsley_et al._2017, title={Design and engineering of water-soluble light-harvesting protein maquettes}, volume={8}, ISSN={["2041-6539"]}, DOI={10.1039/c6sc02417c}, abstractNote={Design of nanometer scale artificial light harvesting and charge separating proteins enables reengineering to overcome the limitations of natural selection for efficient systems that better meet human energetic needs.}, number={1}, journal={CHEMICAL SCIENCE}, author={Kodali, Goutham and Mancini, Joshua A. and Solomon, Lee A. and Episova, Tatiana V. and Roach, Nicholas and Hobbs, Christopher J. and Wagner, Pawel and Mass, Olga A. and Aravindu, Kunche and Barnsley, Jonathan E. and et al.}, year={2017}, month={Jan}, pages={316–324} }
 @article{reddy_zhang_kim_mass_taniguchi_lindsey_2017, title={Synthesis and spectral properties of meso-arylbacteriochlorins, including insights into essential motifs of their hydrodipyrrin precursors}, volume={22}, number={4}, journal={Molecules}, author={Reddy, M. N. and Zhang, S. F. and Kim, H. J. and Mass, O. and Taniguchi, M. and Lindsey, J. S.}, year={2017} }
 @article{zhang_reddy_mass_kim_hu_lindsey_2017, title={Synthesis of tailored hydrodipyrrins and their examination in directed routes to bacteriochlorins and tetradehydrocorrins}, volume={41}, DOI={10.1039/c7nj01892d}, abstractNote={18 gem-dimethyl stabilized hydrodipyrrins with diverse α-substituents have been prepared and examined in directed syntheses of unsymmetrically substituted hydroporphyrins.}, number={19}, journal={New Journal of Chemistry}, author={Zhang, S. F. and Reddy, M. N. and Mass, O. and Kim, H. J. and Hu, G. F. and Lindsey, Jonathan}, year={2017}, pages={11170–11189} }
 @article{tsargorodska_cartron_vasilev_kodali_mass_baumberg_dutton_hunter_torma_leggett_2016, title={Strong Coupling of Localized Surface Plasmons to Excitons in Light-Harvesting Complexes}, volume={16}, ISSN={["1530-6992"]}, DOI={10.1021/acs.nanolett.6b02661}, abstractNote={Gold nanostructure arrays exhibit surface plasmon resonances that split after attaching light harvesting complexes 1 and 2 (LH1 and LH2) from purple bacteria. The splitting is attributed to strong coupling between the localized surface plasmon resonances and excitons in the light-harvesting complexes. Wild-type and mutant LH1 and LH2 from Rhodobacter sphaeroides containing different carotenoids yield different splitting energies, demonstrating that the coupling mechanism is sensitive to the electronic states in the light harvesting complexes. Plasmon–exciton coupling models reveal different coupling strengths depending on the molecular organization and the protein coverage, consistent with strong coupling. Strong coupling was also observed for self-assembling polypeptide maquettes that contain only chlorins. However, it is not observed for monolayers of bacteriochlorophyll, indicating that strong plasmon–exciton coupling is sensitive to the specific presentation of the pigment molecules.}, number={11}, journal={NANO LETTERS}, author={Tsargorodska, Anna and Cartron, Michael L. and Vasilev, Cvetelin and Kodali, Goutham and Mass, Olga A. and Baumberg, Jeremy J. and Dutton, P. Leslie and Hunter, C. Neil and Torma, Paivi and Leggett, Graham J.}, year={2016}, month={Nov}, pages={6850–6856} }
 @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{aravindu_mass_vairaprakash_springer_yang_niedzwiedzki_kirmaier_bocian_holten_lindsey_2013, title={Amphiphilic chlorins and bacteriochlorins in micellar environments. Molecular design, de novo synthesis, and photophysical properties}, volume={4}, number={9}, journal={Chemical Science}, author={Aravindu, K. and Mass, O. and Vairaprakash, P. and Springer, J. W. and Yang, E. and Niedzwiedzki, D. M. and Kirmaier, C. and Bocian, D. F. and Holten, D. and Lindsey, J. S.}, year={2013}, pages={3459–3477} }
 @article{deans_mass_diers_bocian_lindsey_2013, title={Serendipitous synthetic entree to tetradehydro analogues of cobalamins}, volume={37}, number={12}, journal={New Journal of Chemistry}, author={Deans, R. M. and Mass, O. and Diers, J. R. and Bocian, D. F. and Lindsey, J. S.}, year={2013}, pages={3964–3975} }
 @article{springer_faries_diers_muthiah_mass_kee_kirmaier_lindsey_bocian_holten_2012, title={Effects of Substituents on Synthetic Analogs of Chlorophylls. Part 3: The Distinctive Impact of Auxochromes at the 7-versus 3-Positions}, volume={88}, ISSN={["1751-1097"]}, DOI={10.1111/j.1751-1097.2012.01083.x}, abstractNote={Abstract}, number={3}, journal={PHOTOCHEMISTRY AND PHOTOBIOLOGY}, author={Springer, Joseph W. and Faries, Kaitlyn M. and Diers, James R. and Muthiah, Chinnasamy and Mass, Olga and Kee, Hooi Ling and Kirmaier, Christine and Lindsey, Jonathan S. and Bocian, David F. and Holten, Dewey}, year={2012}, pages={651–674} }
 @article{mass_lindsey_2011, title={A trans-AB-Bacteriochlorin Building Block}, volume={76}, ISSN={["1520-6904"]}, DOI={10.1021/jo201967k}, abstractNote={Synthetic bacteriochlorins are of interest for fundamental studies in photochemistry because of their strong absorption in the near-infrared spectral region and close similarity with natural bacteriochlorophylls. A de novo route to 5-methoxybacteriochlorins entails self-condensation of a dihydrodipyrrin-acetal, which in turn is prepared from a 2-(2-nitroethyl)pyrrole species and an α,β-unsaturated ketone-acetal (e.g., 1,1-dimethoxy-4-methylpent-3-en-2-one). Here, four new results are reported concerning the synthesis of substituted bacteriochlorins. First, a new, scalable route to 1,1-dimethoxy-4-methylpent-3-en-2-one removes a significant previous impediment to the overall route. Second, the new route was employed to gain access to new α,β-unsaturated ketones and corresponding dihydrodipyrrins bearing alternative substituents in place of the dimethoxy unit. Third, a dihydrodipyrrin bearing a 1,3-dioxolan-2-yl moiety afforded the bacteriochlorin (30% yield) containing a 2-hydroxyethoxy substituent at the 5-position. Fourth, subsequent bromination proceeded regioselectively at the 15-position to give a trans-(5,15)-AB-bacteriochlorin building block. The linear 5,15-substitution pattern is attractive for a number of molecular designs. The results taken together afford deeper understanding of the scope and limitations of the de novo route and also advance the capabilities for tailoring synthetic bacteriochlorins.}, number={22}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Mass, Olga and Lindsey, Jonathan S.}, year={2011}, month={Nov}, pages={9478–9487} }
 @article{mass_pandithavidana_ptaszek_santiago_springer_jiao_tang_kirmaier_bocian_holten_et al._2011, title={De novo synthesis and properties of analogues of the self-assembling chlorosomal bacteriochlorophylls}, volume={35}, number={11}, journal={New Journal of Chemistry}, author={Mass, O. and Pandithavidana, D. R. and Ptaszek, M. and Santiago, K. and Springer, J. W. and Jiao, J. Y. and Tang, Q. and Kirmaier, C. and Bocian, D. F. and Holten, D. and et al.}, year={2011}, pages={2671–2690} }
 @article{mass_taniguchi_ptaszek_springer_faries_diers_bocian_holten_lindsey_2011, title={Structural characteristics that make chlorophylls green: interplay of hydrocarbon skeleton and substituents}, volume={35}, ISSN={["1369-9261"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-78650499742&partnerID=MN8TOARS}, DOI={10.1039/c0nj00652a}, abstractNote={Understanding the effects of substituents on natural photosynthetic pigments is essential for gaining a deep understanding of why such pigments were selected over the course of evolution for use in photosynthetic systems. This knowledge should provide for a more thoughtful design of artificial light-harvesting systems. The hydrocarbon skeleton of all chlorophylls is phorbine, which contains an annulated five-membered (isocyclic) ring in addition to the reduced pyrrole ring characteristic of chlorins. A phorbine and a 131-oxophorbine (which bears an oxo group in the isocyclic ring) were synthesized as benchmark molecules for fundamental spectral and photophysical studies. The phorbine and 131-oxophorbine macrocycles lack peripheral substituents other than a geminal dimethyl group in the reduced ring to stabilize the chlorin chromophore. The spectral properties and electronic structure of the zinc or free base 131-oxophorbine closely resemble those of the corresponding analogues of chlorophyll a. Accordingly, the fundamental electronic properties of chlorophylls are primarily a consequence of the 131-oxophorbine base macrocycle.}, number={1}, journal={NEW JOURNAL OF CHEMISTRY}, publisher={Royal Society of Chemistry (RSC)}, author={Mass, Olga and Taniguchi, Masahiko and Ptaszek, Marcin and Springer, Joseph W. and Faries, Kaitlyn M. and Diers, James R. and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.}, year={2011}, pages={76–88} }
 @article{lindsey_mass_chen_2011, title={Tapping the near-infrared spectral region with bacteriochlorin arrays}, volume={35}, ISSN={["1144-0546"]}, DOI={10.1039/c0nj00977f}, abstractNote={Bacteriochlorophylls—natural pigments for absorption of near-infrared (NIR) light—underlie light-absorption and energy transduction in photosynthetic bacteria. Capturing and utilizing NIR light is valuable in fields ranging from artificial photosynthesis to photomedicine (photodynamic therapy, imaging, and diagnostics). The desired photochemical features may be best elicited with multicomponent architectures that support efficient excited-state energy and/or electron transfer, yet few such arrays containing bacteriochlorins (the core chromophore of bacteriochlorophylls) are known. This review outlines three synthetic approaches toward bacteriochlorins, surveys all known bacteriochlorin arrays, and compares molecular design strategies for light-harvesting arrays containing bacteriochlorinsversus (the better known) porphyrins.}, number={3}, journal={NEW JOURNAL OF CHEMISTRY}, author={Lindsey, Jonathan S. and Mass, Olga and Chen, Chih-Yuan}, year={2011}, pages={511–516} }
 @article{taniguchi_mass_boyle_tang_diers_bocian_holten_lindsey_2010, title={Structural studies of sparsely substituted synthetic chlorins and phorbines establish benchmarks for changes in the ligand core and framework of chlorophyll macrocycles}, volume={979}, ISSN={["1872-8014"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-77955427819&partnerID=MN8TOARS}, DOI={10.1016/j.molstruc.2010.05.035}, abstractNote={Understanding the changes in molecular structure of tetrapyrrole macrocycles upon derivatization of the organic framework is essential for diverse studies ranging from metal complexation to formation of supramolecular assemblies. New, sparsely substituted free base chlorin, 17-oxochlorin, phorbine and 131-oxophorbine macrocycles provide benchmarks for naturally occurring hydroporphyrins and have been examined here by X-ray crystallography, resonance Raman spectroscopy, and density functional theoretical (DFT) calculations. The macrocycles contain no substituents other than a geminal-dimethyl group attached to the reduced, pyrroline ring. The X-ray studies indicate that the benchmark compounds exhibit only slight distortion from planarity, which increases along the series porphine < chlorin < oxochlorin < phorbine < oxophorbine. The elongated CβCβ bond distance due to sp3 versus sp2 hybridization in the pyrroline ring (ring D) of the (oxo)chlorins and (oxo)phorbines (1.52–1.54 Å) versus that of porphine (1.35 Å) is accompanied by altered bond angles in ring D. Introduction of ring E (exocyclic ring) in a chlorin to give the phorbine or oxophorbine causes alteration of the bond angles at many sites in the framework of the macrocycle; for example, the bond angles of N3C14C15 in the (oxo)phorbine are widened by ∼11° compared to those of porphine or the analogous sparsely substituted chlorin. As a result, the shape of the macrocycle core changes along the series of porphine (nearly square), (oxo)chlorin (kite-shaped), and (oxo)phorbine (right-angled trapezoid), and the core size increases in the order porphine < phorbine ∼ oxophorbine < oxochlorin ∼ chlorin. Comparison of the bond distances and angles in ring E of the phorbine versus oxophorbine indicates that the shortening of the C13C131 bond owing to the presence of the oxo-group is quite small, only 0.024 Å; thus, the unsymmetrical structure of ring E does not appear to be due to conjugation with the C131O group but may be a characteristic feature of the (oxo)phorbine framework. The X-ray data further indicate that the lengths of the oxochlorin C17O and oxophorbine C131O groups are essentially identical, a result also predicted by DFT calculations. Regardless, the observed frequencies for the stretching vibrations of the C17O (1721 cm−1) and C131O (1701 cm−1) groups are different and suggest that conjugation of the latter group with the π-system of the macrocycle is greater than that of the former group. Collectively, the studies provide new insights into the individual factors that give rise to the overall structural characteristics of various macrocycles.}, number={1-3}, journal={JOURNAL OF MOLECULAR STRUCTURE}, publisher={Elsevier BV}, author={Taniguchi, Masahiko and Mass, Olga and Boyle, Paul D. and Tang, Qun and Diers, James R. and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.}, year={2010}, month={Aug}, pages={27–45} }
 @article{mass_ptaszek_taniguchi_diers_kee_bocian_holten_lindsey_2009, title={Synthesis and Photochemical Properties of 12-Substituted versus 13-Substituted Chlorins}, volume={74}, ISSN={["0022-3263"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-68049111576&partnerID=MN8TOARS}, DOI={10.1021/jo900706x}, abstractNote={Understanding the effects of substituents on natural photosynthetic pigments is essential for the rational design of artificial photosynthetic systems. The long-wavelength absorption of chlorins derives from a transition that encompasses rings A and C, which includes the 2,3- and 12,13-positions, respectively. Chlorophylls bear a 3-vinyl group and a 13-keto group, as well as a full complement of substituents at the other beta-pyrrole sites. Prior studies of sparsely substituted synthetic chlorins to probe the effects of substituents yielded 3,13-substituted chlorins that contain a geminal dimethyl group in the pyrroline ring (for stability) and a mesityl group at the 10-position. Attempts to prepare analogous chlorins lacking the 10-mesityl substituent encountered unexpected difficulties during construction of the Eastern half precursor (8,9-dibromo-1-formyldipyrromethane) to the 13-bromochlorin. Direct bromination of 1-formyldipyrromethane with 2 mol equiv of NBS at -78 degrees C led to an isomeric mixture of the desired 8,9-dibromodipyrromethane (minor) and the unexpected 7,9-dibromodipyrromethane (major). Hence, a new rational route was developed for the synthesis of 8,9-dibromo-1-formyldipyrromethane that entailed (i) InCl(3)-catalyzed condensation of 4-bromo-2-(hydroxymethyl)pyrrole and pyrrole to give the 8-bromodipyrromethane, (ii) 1-formylation, and (iii) 9-bromination. Two new substituted chlorins carrying auxochromes at the 3- and 13-positions were synthesized. The photophysical and redox properties of the 13-substituted chlorins were compared with those of isomeric 12-substituted chlorins, synthesized previously via a 7,9-dibromo-1-formyldipyrromethane. Such studies (static absorption and fluorescence spectroscopy, time-resolved fluorescence spectroscopy, electrochemistry of the zinc chelates, and density functional theoretical calculations) reveal only very slight differences between the isomeric 12- and 13-substituted chlorins.}, number={15}, journal={JOURNAL OF ORGANIC CHEMISTRY}, publisher={American Chemical Society (ACS)}, author={Mass, Olga and Ptaszek, Marcin and Taniguchi, Masahiko and Diers, James R. and Kee, Hooi Ling and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.}, year={2009}, month={Aug}, pages={5276–5289} }