@article{jing_liu_jiang_tran_rong_wang_lindsey_2022, title={Meso bromination and derivatization of synthetic bacteriochlorins}, volume={46}, ISSN={["1369-9261"]}, DOI={10.1039/d1nj05853c}, abstractNote={Twelve bacteriochlorin building blocks featuring meso-substitution have been prepared including a set with finely tuned long-wavelength absorption (725–757 nm) for studies in photonics.}, number={12}, journal={NEW JOURNAL OF CHEMISTRY}, author={Jing, Haoyu and Liu, Sijia and Jiang, Jianbing and Tran, Vy-Phuong and Rong, Jie and Wang, Pengzhi and Lindsey, Jonathan S.}, year={2022}, month={Mar}, pages={5556–5572} }
 @article{jing_wang_chen_jiang_vairaprakash_liu_rong_chen_nalaoh_lindsey_2022, title={Synthesis of bacteriochlorins bearing diverse beta-substituents}, volume={3}, ISSN={["1369-9261"]}, DOI={10.1039/d1nj05852e}, abstractNote={Eleven bacteriochlorins have been prepared for surface attachment, bioconjugation, water-solubilization, vibrational studies, and elaboration into multichromophore arrays.}, journal={NEW JOURNAL OF CHEMISTRY}, author={Jing, Haoyu and Wang, Pengzhi and Chen, Boyang and Jiang, Jianbing and Vairaprakash, Pothiappan and Liu, Sijia and Rong, Jie and Chen, Chih-Yuan and Nalaoh, Phattananawee and Lindsey, Jonathan S.}, year={2022}, month={Mar} }
 @article{fujita_jing_krayer_allu_veeraraghavaiah_wu_jiang_diers_magdaong_mandal_et al._2019, title={Annulated bacteriochlorins for near- infrared photophysical studies}, volume={43}, ISSN={["1369-9261"]}, DOI={10.1039/c9nj01113g}, abstractNote={Bacteriochlorins with phenaleno or benzo annulation absorb at 913 or 1033 nm and exhibit excited-state lifetimes of 150 or 7 ps, suggesting applications in photoacoustic imaging.}, number={19}, journal={NEW JOURNAL OF CHEMISTRY}, author={Fujita, Hikaru and Jing, Haoyu and Krayer, Michael and Allu, Srinivasarao and Veeraraghavaiah, Gorre and Wu, Zhiyuan and Jiang, Jianbing and Diers, James R. and Magdaong, Nikki Cecil M. and Mandal, Amit K. and et al.}, year={2019}, month={May}, pages={7209–7232} }
 @article{jiang_matula_swierk_romano_wu_batista_crabtree_lindsey_wang_brudvig_2018, title={Unusual Stability of a Bacteriochlorin Electrocatalyst under Reductive Conditions. A Case Study on CO2 Conversion to CO}, volume={8}, ISSN={["2155-5435"]}, DOI={10.1021/acscatal.8b02991}, abstractNote={Photosynthetic CO2 fixation is mediated by the enzyme RuBisCo, which employs a nonredox-active metal (Mg2+) to bind CO2 adjacent to an organic ligand that provides reducing equivalents for CO2 fixa...}, number={11}, journal={ACS CATALYSIS}, author={Jiang, Jianbing and Matula, Adam J. and Swierk, John R. and Romano, Neyen and Wu, Yueshen and Batista, Victor S. and Crabtree, Robert H. and Lindsey, Jonathan S. and Wang, Hailiang and Brudvig, Gary W.}, year={2018}, month={Nov}, pages={10131–10136} }
 @article{mancini_kodali_jiang_reddy_lindsey_bryant_dutton_moser_2017, title={Multi-step excitation energy transfer engineered in genetic fusions of natural and synthetic light-harvesting proteins}, volume={14}, number={127}, journal={Journal of the Royal Society Interface}, author={Mancini, J. A. and Kodali, G. and Jiang, J. B. and Reddy, K. R. and Lindsey, J. S. and Bryant, D. A. and Dutton, P. L. and Moser, C. C.}, year={2017} }
 @article{zhang_jiang_liu_taniguchi_mandal_evans-storms_pitner_bocian_holten_lindsey_2016, title={Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, near-infrared-emitting bacteriochlorins}, volume={40}, ISSN={["1369-9261"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-84984904482&partnerID=MN8TOARS}, DOI={10.1039/c6nj01155a}, abstractNote={PEGylated bacteriochlorins are soluble in water, can be excited in the ultraviolet, and exhibit a narrow fluorescence band in the NIR spectral region.}, number={9}, journal={NEW JOURNAL OF CHEMISTRY}, author={Zhang, Nuonuo and Jiang, Jianbing and Liu, Mengran and Taniguchi, Masahiko and Mandal, Amit Kumar and Evans-Storms, Rosemary B. and Pitner, J. Bruce and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.}, year={2016}, pages={7750–7767} }
 @article{zhang_reddy_jiang_taniguchi_sommer_lindsey_2015, title={Elaboration of an unexplored substitution site in synthetic bacteriochlorins}, volume={19}, ISSN={["1099-1409"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-84937975805&partnerID=MN8TOARS}, DOI={10.1142/s1088424615500534}, abstractNote={ The ability to introduce substituents at designated sites about the perimeter of synthetic bacteriochlorins – analogs of bacteriochlorophylls of bacterial photosynthesis – remains a subject of ongoing study. Here, the self-condensation of a dihydrodipyrrin-dioxolane affords a 5-[2-(trimethylsiloxy)ethoxy]bacteriochlorin. Like a 5-methoxybacteriochlorin, the latter undergoes regioselective bromination at the 15-position, directed by the distal 5-alkoxy group. On the other hand, attempted bromination of a bacteriochlorin bearing a 5-(2-hydroxyethoxy) group resulted in intramolecular ether formation with the adjacent β-pyrroline position to give an annulated dioxepine ring (confirmed by single-crystal X-ray structural analysis). The hydroxyethoxy group at the 5-position can be derivatized by acylation. In addition, the installation of auxochromes (methoxycarbonyl, phenylethynyl) at the β-pyrrole rings causes a substantial bathochromic shift of the long-wavelength absorption band (812 nm) and companion fluorescence emission band (821 nm). Taken together, the modification of the 5-substituent complements existing methods for installing a single substituent on the bacteriochlorin macrocycle. }, number={7}, journal={JOURNAL OF PORPHYRINS AND PHTHALOCYANINES}, publisher={World Scientific Pub Co Pte Lt}, author={Zhang, Nuonuo and Reddy, Kanumuri Ramesh and Jiang, Jianbing and Taniguchi, Masahiko and Sommer, Roger D. and Lindsey, Jonathan S.}, year={2015}, month={Jul}, pages={887–902} }
 @article{jiang_taniguchi_lindsey_2015, title={Near-infrared tunable bacteriochlorins equipped for bioorthogonal labeling}, volume={39}, ISSN={["1369-9261"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-84930627951&partnerID=MN8TOARS}, DOI={10.1039/c5nj00209e}, abstractNote={Nine new near-infrared absorbing (729–820 nm) synthetic bacteriochlorins are equipped with one of four reactive groups for bioorthogonal conjugation.}, number={6}, journal={NEW JOURNAL OF CHEMISTRY}, publisher={Royal Society of Chemistry (RSC)}, author={Jiang, Jianbing and Taniguchi, Masahiko and Lindsey, Jonathan S.}, year={2015}, pages={4534–4550} }
 @article{jiang_chen_zhang_vairaprakash_lindsey_2015, title={Polarity-tunable and wavelength-tunable bacteriochlorins bearing a single carboxylic acid or NHS ester. Use in a protein bioconjugation model system}, volume={39}, ISSN={["1369-9261"]}, DOI={10.1039/c4nj01340a}, abstractNote={10 new near-infrared absorbing bacteriochlorins (soluble in aqueous or membranous media) are equipped for protein bioconjugation.}, number={1}, journal={NEW JOURNAL OF CHEMISTRY}, author={Jiang, Jianbing and Chen, Chih-Yuan and Zhang, Nuonuo and Vairaprakash, Pothiappan and Lindsey, Jonathan S.}, year={2015}, month={Jan}, pages={403–419} }
 @article{jiang_yang_reddy_niedzwiedzki_kirmaier_bocian_holten_lindsey_2015, title={Synthetic bacteriochlorins bearing polar motifs (carboxylate, phosphonate, ammonium and a short PEG). Water-solubilization, bioconjugation, and photophysical properties}, volume={39}, ISSN={["1369-9261"]}, DOI={10.1039/c5nj00759c}, abstractNote={A bacteriochlorin scaffold has been derivatized for life sciences applications.}, number={7}, journal={NEW JOURNAL OF CHEMISTRY}, author={Jiang, Jianbing and Yang, Eunkyung and Reddy, Kanumuri Ramesh and Niedzwiedzki, Dariusz M. and Kirmaier, Christine and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.}, year={2015}, pages={5694–5714} }
 @article{jiang_reddy_pavan_lubian_harris_jiao_niedzwiedzki_kirmaier_parkes-loach_loach_et al._2014, title={Amphiphilic, hydrophilic, or hydrophobic synthetic bacteriochlorins in biohybrid light-harvesting architectures: consideration of molecular designs}, volume={122}, ISSN={["1573-5079"]}, DOI={10.1007/s11120-014-0021-9}, abstractNote={Biohybrid light-harvesting architectures can be constructed that employ native-like bacterial photosynthetic antenna peptides as a scaffold to which synthetic chromophores are attached to augment overall spectral coverage. Synthetic bacteriochlorins are attractive to enhance capture of solar radiation in the photon-rich near-infrared spectral region. The effect of the polarity of the bacteriochlorin substituents on the antenna self-assembly process was explored by the preparation of a bacteriochlorin-peptide conjugate using a synthetic amphiphilic bacteriochlorin (B1) to complement prior studies using hydrophilic (B2, four carboxylic acids) or hydrophobic (B3) bacteriochlorins. The amphiphilic bioconjugatable bacteriochlorin B1 with a polar ammonium-terminated tail was synthesized by sequential Pd-mediated reactions of a 3,13-dibromo-5-methoxybacteriochlorin. Each bacteriochlorin bears a maleimido-terminated tether for attachment to a cysteine-containing analog of the Rhodobacter sphaeroides antenna β-peptide to give conjugates β-B1, β-B2, and β-B3. Given the hydrophobic nature of the β-peptide, the polarity of B1 and B2 facilitated purification of the respective conjugate compared to the hydrophobic B3. Bacteriochlorophyll a (BChl a) associates with each conjugate in aqueous micellar media to form a dyad containing two β-peptides, two covalently attached synthetic bacteriochlorins, and a datively bonded BChl-a pair, albeit to a limited extent for β-B2. The reversible assembly/disassembly of dyad (β-B2/BChl)2 was examined in aqueous detergent (octyl glucoside) solution by temperature variation (15-35 °C). The energy-transfer efficiency from the synthetic bacteriochlorin to the BChl-a dimer was found to be 0.85 for (β-B1/BChl)2, 0.40 for (β-B2/BChl)2, and 0.85 for (β-B3/BChl)2. Thus, in terms of handling, assembly and energy-transfer efficiency taken together, the amphiphilic design examined herein is more attractive than the prior hydrophilic or hydrophobic designs.}, number={2}, journal={PHOTOSYNTHESIS RESEARCH}, author={Jiang, Jianbing and Reddy, Kanumuri Ramesh and Pavan, M. Phani and Lubian, Elisa and Harris, Michelle A. and Jiao, Jieying and Niedzwiedzki, Dariusz M. and Kirmaier, Christine and Parkes-Loach, Pamela S. and Loach, Paul A. and et al.}, year={2014}, month={Nov}, pages={187–202} }
 @article{harris_sahin_jiang_vairaprakash_parkes-loach_niedzwiedzki_kirmaier_loach_bocian_holten_et al._2014, title={Enhanced Light-Harvesting Capacity by Micellar Assembly of Free Accessory Chromophores and LH1-like Antennas}, volume={90}, ISSN={["1751-1097"]}, DOI={10.1111/php.12319}, abstractNote={Abstract}, number={6}, journal={PHOTOCHEMISTRY AND PHOTOBIOLOGY}, author={Harris, Michelle A. and Sahin, Tuba and Jiang, Jianbing and Vairaprakash, Pothiappan and Parkes-Loach, Pamela S. and Niedzwiedzki, Dariusz M. and Kirmaier, Christine and Loach, Paul A. and Bocian, David F. and Holten, Dewey and et al.}, year={2014}, pages={1264–1276} }
 @article{jiang_vairaprakash_reddy_sahin_pavan_lubian_lindsey_2014, title={Hydrophilic tetracarboxy bacteriochlorins for photonics applications}, volume={12}, ISSN={["1477-0539"]}, DOI={10.1039/c3ob41791c}, abstractNote={Bacteriochlorins absorb strongly in the near-infrared (NIR, 700-900 nm) region and hence are well suited for photophysical studies and photomedical applications, yet such endeavors heretofore have been largely limited by the intrinsic lipophilicity of the bacteriochlorin macrocycle. Here, a new molecular design is investigated wherein 3,5-dicarboxyphenyl units are appended to the β-pyrrolic positions of the bacteriochlorin. Use of the 3,5-aryl substitution motif places the carboxylic acid groups, which are anionic at neutral pH, above and below the plane of the bacteriochlorin macrocycle. A de novo synthesis has been employed to create five such bacteriochlorins, which uses as intermediates two new 2,12-dibromobacteriochlorin building blocks and a known 3,13-dibromobacteriochlorin. The aryl groups with protected carboxylate moieties were introduced by Suzuki coupling; subsequent deprotection afforded the hydrophilic bacteriochlorins. The latter were characterized by absorption and fluorescence spectroscopy in DMF and in aqueous phosphate buffer (pH 7). In most cases, comparable sharp emission (FWHM of ∼25 nm) and modest fluorescence yields (0.060-0.11) were observed in aqueous phosphate buffer medium and in DMF. Aqueous solubility was examined by absorption spectral interrogation of samples over a 1000-fold concentration range with reciprocal change in pathlength (∼0.5, 5, 50, and 500 μM; 10, 1, 0.1, and 0.01 cm pathlength cuvettes). One hydrophilic bacteriochlorin was prepared that contains a single maleimido-terminated tether for bioconjugation; the tether was installed by the sequence of 15-bromination of the bacteriochlorin, Suzuki coupling, and DCC-mediated amide formation. The maleimido-bacteriochlorin was conjugated to a 48-residue cysteine-containing peptide analogue of a constituent from a bacterial photosynthetic light-harvesting complex. Taken together, the results show a new molecular design and facile de novo synthetic route for obtaining hydrophilic bacteriochlorins including a bioconjugatable group if desired.}, number={1}, journal={ORGANIC & BIOMOLECULAR CHEMISTRY}, author={Jiang, Jianbing and Vairaprakash, Pothiappan and Reddy, Kanumuri Ramesh and Sahin, Tuba and Pavan, M. Phani and Lubian, Elisa and Lindsey, Jonathan S.}, year={2014}, month={Jan}, pages={86–103} }
 @article{harris_jiang_niedzwiedzki_jiao_taniguchi_kirmaier_loach_bocian_lindsey_holten_et al._2014, title={Versatile design of biohybrid light-harvesting architectures to tune location, density, and spectral coverage of attached synthetic chromophores for enhanced energy capture}, volume={121}, ISSN={["1573-5079"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-84902249655&partnerID=MN8TOARS}, DOI={10.1007/s11120-014-9993-8}, abstractNote={Biohybrid antennas built upon chromophore-polypeptide conjugates show promise for the design of efficient light-capturing modules for specific purposes. Three new designs, each of which employs analogs of the β-polypeptide from Rhodobacter sphaeroides, have been investigated. In the first design, amino acids at seven different positions on the polypeptide were individually substituted with cysteine, to which a synthetic chromophore (bacteriochlorin or Oregon Green) was covalently attached. The polypeptide positions are at -2, -6, -10, -14, -17, -21, and -34 relative to the 0-position of the histidine that coordinates bacteriochlorophyll a (BChl a). All chromophore-polypeptides readily formed LH1-type complexes upon combination with the α-polypeptide and BChl a. Efficient energy transfer occurs from the attached chromophore to the circular array of 875 nm absorbing BChl a molecules (denoted B875). In the second design, use of two attachment sites (positions -10 and -21) on the polypeptide affords (1) double the density of chromophores per polypeptide and (2) a highly efficient energy-transfer relay from the chromophore at -21 to that at -10 and on to B875. In the third design, three spectrally distinct bacteriochlorin-polypeptides were prepared (each attached to cysteine at the -14 position) and combined in an ~1:1:1 mixture to form a heterogeneous mixture of LH1-type complexes with increased solar coverage and nearly quantitative energy transfer from each bacteriochlorin to B875. Collectively, the results illustrate the great latitude of the biohybrid approach for the design of diverse light-harvesting systems.}, number={1}, journal={PHOTOSYNTHESIS RESEARCH}, author={Harris, Michelle A. and Jiang, Jianbing and Niedzwiedzki, Dariusz M. and Jiao, Jieying and Taniguchi, Masahiko and Kirmaier, Christine and Loach, Paul A. and Bocian, David F. and Lindsey, Jonathan S. and Holten, Dewey and et al.}, year={2014}, month={Jul}, pages={35–48} }
 @article{harris_parkes-loach_springer_jiang_martin_qian_jiao_niedzwiedzki_kirmaier_olsen_et al._2013, title={Integration of multiple chromophores with native photosynthetic antennas to enhance solar energy capture and delivery}, volume={4}, number={10}, journal={Chemical Science}, author={Harris, M. A. and Parkes-Loach, P. S. and Springer, J. W. and Jiang, J. B. and Martin, E. C. and Qian, P. and Jiao, J. Y. and Niedzwiedzki, D. M. and Kirmaier, C. and Olsen, J. D. and et al.}, year={2013}, pages={3924–3933} }
 @article{reddy_jiang_krayer_harris_springer_yang_jiao_niedzwiedzki_pandithavidana_parkes-loach_et al._2013, title={Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures}, volume={4}, number={5}, journal={Chemical Science}, author={Reddy, K. R. and Jiang, J. B. and Krayer, M. and Harris, M. A. and Springer, J. W. and Yang, E. and Jiao, J. Y. and Niedzwiedzki, D. M. and Pandithavidana, D. and Parkes-Loach, P. S. and et al.}, year={2013}, pages={2036–2053} }