@article{liu_chen_hood_taniguchi_diers_bocian_holten_lindsey_2017, title={Synthesis, photophysics and electronic structure of oxobacteriochlorins}, volume={41}, ISSN={["1369-9261"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-85022033561&partnerID=MN8TOARS}, DOI={10.1039/c6nj04135c}, abstractNote={Synthetic oxobacteriochlorins exhibit strong absorption in the deep-red window flanked by chlorins to the red and bacteriochlorins to the near-infrared.}, number={10}, journal={NEW JOURNAL OF CHEMISTRY}, publisher={Royal Society of Chemistry (RSC)}, author={Liu, Mengran and Chen, Chih-Yuan and Hood, Don and Taniguchi, Masahiko and Diers, James R. and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.}, year={2017}, month={May}, pages={3732–3744} }
 @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={Synthetic bacteriochlorins absorb in the near-infrared (NIR) region and are versatile analogues of natural bacteriochlorophylls. The utilization of these chromophores in energy sciences and photomedicine requires the ability to tailor their physicochemical properties, including the incorporation of units to impart water solubility. Herein, we report the synthesis, from two common bacteriochlorin building blocks, of five wavelength-tunable, bioconjugatable and water-soluble bacteriochlorins along with two non-bioconjugatable benchmarks. Each bacteriochlorin bears short polyethylene glycol (PEG) units as the water-solubilizing motif. The PEG groups are located at the 3,5-positions of aryl groups at the pyrrolic β-positions to suppress aggregation in aqueous media. A handle containing a single carboxylic acid is incorporated to allow bioconjugation. The seven water-soluble bacteriochlorins in water display Qy absorption into the NIR range (679-819 nm), sharp emission (21-36 nm full-width-at-half-maximum) and modest fluorescence quantum yield (0.017-0.13). Each bacteriochlorin is neutral (non-ionic) yet soluble in organic (e.g., CH2Cl2, DMF) and aqueous solutions. Water solubility was assessed using absorption spectroscopy by changing the concentration ∼1000-fold (190-690 µM to 0.19-0.69 µM) with a reciprocal change in pathlength (0.1-10 cm). All bacteriochlorins showed excellent solubility in water, except for a bacteriochlorin-imide that gave slight aggregation at higher concentrations. One bacteriochlorin was conjugated to a mouse polyclonal IgG antibody for use in flow cytometry with compensation beads for proof-of-principle. The antibody conjugate of B2-NHS displayed a sharp signal upon ultraviolet laser excitation (355 nm) with NIR emission measured with a 730/45 nm bandpass filter. Overall, the study gives access to a set of water-soluble bacteriochlorins with desirable photophysical properties for use in multiple fields.}, 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{liu_chen_mandal_chandrashaker_evans-storms_pitner_bocian_holten_lindsey_2016, title={Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, red-emitting chlorins}, volume={40}, ISSN={["1369-9261"]}, DOI={10.1039/c6nj01154c}, abstractNote={Chromophores that absorb and emit in the red spectral region (600-700 nm), are water soluble, and bear a bioconjugatable tether are relatively rare yet would fulfill many applications in photochemistry and photomedicine. Here, three molecular designs have been developed wherein stable synthetic chlorins - analogues of chlorophylls - have been tailored with PEG groups for use in aqueous solution. The designs differ with regard to order of the installation (pre/post-formation of the chlorin macrocycle) and position of the PEG groups. Six PEGylated synthetic chlorins (three free bases, three zinc chelates) have been prepared, of which four are equipped with a bioconjugatable (carboxylic acid) tether. The most effective design for aqueous solubilization entails facial encumbrance where PEG groups project above and below the plane of the hydrophobic disk-like chlorin macrocycle. The chlorins possess strong absorption at ~400 nm (B band) and in the red region (Qy band); regardless of wavelength of excitation, emission occurs in the red region. Excitation in the ~400 nm region thus provides an effective Stokes shift of >200 nm. The four bioconjugatable water-soluble chlorins exhibit Qy absorption/emission in water at 613/614, 636/638, 698/700 and 706/710 nm. The spectral properties are essentially unchanged in DMF and water for the facially encumbered chlorins, which also exhibit narrow Qy absorption and emission bands (full-width-at-half maximum of each <25 nm). The water-solubility was assessed by absorption spectroscopy over the concentration range ~0.4 μM - 0.4 mM. One chlorin was conjugated to a mouse polyclonal IgG antibody for use in flow cytometry with compensation beads for proof-of-principle. The conjugate displayed a sharp signal when excited by a violet laser (405 nm) with emission in the 620-660 nm range. Taken together, the designs described herein augur well for development of a set of spectrally distinct chlorins with relatively sharp bands in the red region.}, number={9}, journal={NEW JOURNAL OF CHEMISTRY}, author={Liu, Mengran and Chen, Chih-Yuan and Mandal, Amit Kumar and Chandrashaker, Vanampally and Evans-Storms, Rosemary B. and Pitner, J. Bruce and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.}, year={2016}, pages={7721–7740} }
 @article{mandal_sahin_liu_lindsey_bocian_holten_2016, title={Photophysical comparisons of PEGylated porphyrins, chlorins and bacteriochlorins in water}, volume={40}, ISSN={["1369-9261"]}, DOI={10.1039/c6nj02091g}, abstractNote={Synthesis of a bioconjugatable water-soluble (PEGylated) <italic>trans</italic>-AB-porphyrin enables photophysical comparisons (<italic>τ</italic><sub>S</sub>, <italic>k</italic><sub>f</sub>, <italic>k</italic><sub>ic</sub>, <italic>k</italic><sub>isc</sub>, <italic>Φ</italic><sub>f</sub>, <italic>Φ</italic><sub>ic</sub>, <italic>Φ</italic><sub>isc</sub>) with analogous chlorins and bacteriochlorins in DMF and water.}, number={11}, journal={NEW JOURNAL OF CHEMISTRY}, author={Mandal, Amit Kumar and Sahin, Tuba and Liu, Mengran and Lindsey, Jonathan S. and Bocian, David F. and Holten, Dewey}, year={2016}, pages={9648–9656} }
 @article{yuen_harris_liu_diers_kirmaier_bocian_lindsey_holten_2015, title={Effects of Substituents on Synthetic Analogs of Chlorophylls. Part 4: How Formyl Group Location Dictates the Spectral Properties of Chlorophylls b, d and f}, volume={91}, ISSN={["1751-1097"]}, DOI={10.1111/php.12401}, abstractNote={Photosynthetic organisms are adapted to light characteristics in their habitat in part via the spectral characteristics of the associated chlorophyll pigments, which differ in the position of a formyl group around the chlorin macrocycle (chlorophylls b, d, f) or no formyl group (chlorophyll a). To probe the origin of this spectral tuning, the photophysical and electronic structural properties of a new set of synthetic chlorins are reported. The zinc and free base chlorins have a formyl group at either the 2- or 3-position. The four compounds have fluorescence yields in the range 0.19-0.28 and singlet excited-state lifetimes of ca 4 ns for zinc chelates and ca 8 ns for the free base forms. The photophysical properties of the 2- and 3-formyl zinc chlorins are similar to those observed previously for 13-formyl or 3,13-diformyl chlorins, but differ markedly from those for 7-formyl analogs. Molecular-orbital characteristics obtained from density functional theory (DFT) calculations were used as input to spectral simulations employing the four-orbital model. The analysis has uncovered the key changes in electronic structure engendered by the presence/location of a formyl group at various macrocycle positions, which is relevant to understanding the distinct spectral properties of the natural chlorophylls a, b, d and f.}, number={2}, journal={PHOTOCHEMISTRY AND PHOTOBIOLOGY}, author={Yuen, Jonathan M. and Harris, Michelle A. and Liu, Mengran and Diers, James R. and Kirmaier, Christine and Bocian, David F. and Lindsey, Jonathan S. and Holten, Dewey}, year={2015}, pages={331–342} }
 @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} }