@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{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{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={PEGylated chlorins are soluble in water, can be excited in the near-ultraviolet, and exhibit a relatively narrow fluorescence band in the red spectral 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{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{chen_taniguchi_lindsey_2014, title={NMR spectral properties of 16 synthetic bacteriochlorins with site-specific C-13 or N-15 substitution}, volume={18}, ISSN={["1099-1409"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-84903791617&partnerID=MN8TOARS}, DOI={10.1142/s1088424614500199}, abstractNote={ The 1 H , 13 C , and 15 N nuclear magnetic resonance (NMR) spectral properties have been examined of a family of synthetic bacteriochlorins wherein each member incorporates a pair of 13 C or 15 N atoms. The atom locations span the inner core of the macrocycle: (1) 15 N at the 21,23- or 22,24-positions; (2) 13 C at the meso- (5,15- or 10,20-) positions; (3) 13 C at the pyrrole α-positions (1,11- or 4,14-positions); and (4) 13 C at the pyrroline α-positions (6,16- or 9,19-positions). Each bacteriochlorin lacks peripheral substituents other than a geminal dimethyl group at the 8- and 18-positions to preclude adventitious dehydrogenation. In total, eight free base and eight zinc bacteriochlorin isotopologs were examined to directly assign 1 H , 13 C and 15 N resonances of the macrocycle skeleton. Complete and unambiguous assignments, including those for all tertiary and quaternary carbons, were accomplished chiefly by direct inspection of 1D NMR spectra of each isotopolog. Coupling constants (1 H –1 H , 13 C –1 H , 15 N –1 H , 13 C –13 C and 15 N –13 C ), which are rarely reported for tetrapyrroles, also were extracted. The 1 H and 13 C chemical shifts were then compared to those of unsaturated analogs (chlorin, porphyrin) and natural bacteriochlorophylls. The comprehensive set of NMR spectroscopic properties of sparsely substituted bacteriochlorins provides valuable information for understanding substitution effects and aromaticity in structurally more elaborate counterparts. }, number={6}, journal={JOURNAL OF PORPHYRINS AND PHTHALOCYANINES}, publisher={World Scientific Pub Co Pte Lt}, author={Chen, Chih-Yuan and Taniguchi, Masahiko and Lindsey, Jonathan S.}, year={2014}, month={Jun}, pages={433–456} }
 @article{chen_bocian_lindsey_2014, title={Synthesis of 24 Bacteriochlorin Isotopologues, Each Containing a Symmetrical Pair of C-13 or N-15 Atoms in the Inner Core of the Macrocycle}, volume={79}, ISSN={["0022-3263"]}, DOI={10.1021/jo402488n}, abstractNote={Synthetic bacteriochlorins containing site-specific isotopic substitution enable spectroscopic interrogation to delineate physicochemical features relevant to bacteriochlorophylls in photosynthesis but have been little explored. A de novo synthesis has been employed to prepare bacteriochlorins wherein each macrocycle contains a pair of (13)C or (15)N atoms yet lacks substituents other than a geminal dimethyl group in each pyrroline ring. Preparation of a dihydrodipyrrin–acetal with single-isotopic substitution gives rise to a bacteriochlorin that contains two isotopic substitutions symmetrically disposed by a 180° rotation about the normal to the plane of the macrocycle. Eight such isotopically substituted bacteriochlorins were prepared from commercially available reactants (bacteriochlorin sites): ((13)C)paraformaldehyde (1, 11); ((13)C)formamide (4, 14); triethyl ((13)C)orthoformate (5, 15); K(13)CN (6, 16); (13)CH3NO2 (9, 19); N,N-dimethyl((13)C)formamide (10, 20); ((15)N)pyrrole (21, 23); CH3(15)NO2 (22, 24). Some loss of (15)N upon TiCl3-mediated McMurry-type ring closure of a nitro((15)N)hexanone is attributed to a parallel sequence of three reactions (Nef, exchange with natural-abundance NH4OAc buffer, and Paal–Knorr ring closure) leading to the dihydrodipyrrin–acetal. Zinc and copper chelates of each bacteriochlorin also were prepared. Together, the 24 bacteriochlorin isotopologues should provide valuable benchmarks for understanding ground- and excited-state molecular physics of the macrocycles related to photosynthetic function of bacteriochlorophylls.}, number={3}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Chen, Chih-Yuan and Bocian, David F. and Lindsey, Jonathan S.}, year={2014}, month={Feb}, pages={1001–1016} }
 @article{diers_tang_hondros_chen_holten_lindsey_bocian_2014, title={Vibronic Characteristics and Spin-Density Distributions in Bacteriochlorins as Revealed by Spectroscopic Studies of 16 Isotopologues. Implications for Energy- and Electron-Transfer in Natural Photosynthesis and Artificial Solar-Energy Conversion}, volume={118}, ISSN={["1520-5207"]}, DOI={10.1021/jp504286w}, abstractNote={Vibronic characteristics and spin-density distributions in the core bacteriochlorin macrocycle were revealed by spectroscopic and theoretical studies of 16 isotopologues. The vibrational modes in copper bacteriochlorin isotopologues were examined via resonance Raman and Fourier-transform infrared spectroscopy. The resonance Raman spectra exhibit an exceptional sparcity of vibronically active modes of the core macrocycle, in contrast with the rich spectra of the natural bacteriochlorophylls. The Qy-excitation resonance Raman spectrum is dominated by a single mode at 727 cm-1, which calculations suggest is due to a symmetrical accordion-like deformation of the five-atom Cm(CaNCa)pyrroleCm portion of the ring core. This deformation also dominates the vibronic features in the absorption and fluorescence spectra. The spin-density distributions in the π-cation radical of the zinc bacteriochlorin isotopologues were studied by electron paramagnetic resonance spectroscopy. The spectra indicate a significant electron/spin density (ρ ∼ 0.1) on each meso-carbon atom. This observation contradicts the predictions of early calculations that have been assumed to be correct for nearly four decades. Collectively, these findings have implications for how the structural features that characterize natural bacteriochlorophylls might influence energy- and electron-transfer processes in photosynthesis and alter the thinking on the design of synthetic, bacteriochlorin-based arrays for solar-energy conversion.}, number={27}, journal={JOURNAL OF PHYSICAL CHEMISTRY B}, author={Diers, James R. and Tang, Qun and Hondros, Christopher J. and Chen, Chih-Yuan and Holten, Dewey and Lindsey, Jonathan S. and Bocian, David F.}, year={2014}, month={Jul}, pages={7520–7532} }
 @article{sun_chen_lindsey_2013, title={Synthesis and characterization of lipophilic, near-IR absorbing metallobacteriochlorins}, volume={34}, number={4}, journal={Chemical Journal of Chinese Universities}, author={Sun, E. J. and Chen, C. Y. and Lindsey, J. S.}, year={2013}, pages={776–781} }
 @article{chen_sun_fan_taniguchi_mcdowell_yang_diers_bocian_holten_lindsey_2012, title={Synthesis and Physicochemical Properties of Metallobacteriochlorins}, volume={51}, ISSN={["1520-510X"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-84865712494&partnerID=MN8TOARS}, DOI={10.1021/ic301262k}, abstractNote={Access to metallobacteriochlorins is essential for investigation of a wide variety of fundamental photochemical processes, yet relatively few synthetic metallobacteriochlorins have been prepared. Members of a set of synthetic bacteriochlorins bearing 0-4 carbonyl groups (1, 2, or 4 carboethoxy substituents, or an annulated imide moiety) were examined under two conditions: (i) standard conditions for zincation of porphyrins [Zn(OAc)(2)·2H(2)O in N,N-dimethylformamide (DMF) at 60-80 °C], and (ii) treatment in tetrahydrofuran (THF) with a strong base [e.g., NaH or lithium diisopropylamide (LDA)] followed by a metal reagent MX(n). Zincation of bacteriochlorins that bear 2-4 carbonyl groups proceeded under the former method whereas those with 0-2 carbonyl groups proceeded with NaH or LDA/THF followed by Zn(OTf)(2). The scope of metalation (via NaH or LDA in THF) is as follows: (a) for bacteriochlorins that bear two electron-releasing aryl groups, M = Cu, Zn, Pd, and InCl (but not Mg, Al, Ni, Sn, or Au); (b) for bacteriochlorins that bear two carboethoxy groups, M = Ni, Cu, Zn, Pd, Cd, InCl, and Sn (but not Mg, Al, or Au); and (c) a bacteriochlorin with four carboethoxy groups was metalated with Mg (other metals were not examined). Altogether, 15 metallobacteriochlorins were isolated and characterized. Single-crystal X-ray analysis of 8,8,18,18-tetramethylbacteriochlorin reveals the core geometry provided by the four nitrogen atoms is rectangular; the difference in length of the two sides is ∼0.08 Å. Electronic characteristics of (metal-free) bacteriochlorins were probed through electrochemical measurements along with density functional theory calculation of the energies of the frontier molecular orbitals. The photophysical properties (fluorescence yields, triplet yields, singlet and triplet excited-state lifetimes) of the zinc bacteriochlorins are generally similar to those of the metal-free analogues, and to those of the native chromophores bacteriochlorophyll a and bacteriopheophytin a. The availability of diverse metallobacteriochlorins should prove useful in a variety of fundamental photochemical studies and applications.}, number={17}, journal={INORGANIC CHEMISTRY}, publisher={American Chemical Society (ACS)}, author={Chen, Chih-Yuan and Sun, Erjun and Fan, Dazhong and Taniguchi, Masahiko and McDowell, Brian E. and Yang, Eunkyung and Diers, James R. and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.}, year={2012}, month={Sep}, pages={9443–9464} }
 @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} }