About

Jonathan Lindsey is a professor and the Glaxo Distinguished University Chair at NC State University, based in the Department of Chemistry. He holds a B.S. in Chemistry with Distinction and Honors from Indiana University, obtained in 1978, and a Ph.D. in Chemistry from The Rockefeller University, completed in 1983. Following his doctoral studies, he was a Postdoctoral Fellow at The Rockefeller University in 1984. His research focuses on organic chemistry for cancer diagnosis and novel therapeutics, studies of organic natural product biodiversity in cyanobacteria, and synthetic tetrapyrrole chemistry including chlorophylls. His work is associated with the fields of chemical biology, drug discovery, energy, and organic chemistry, contributing to the understanding and development of organic compounds with biomedical applications.

Research topics

• Physics
• Chemistry
• Optics
• Organic chemistry
• Photochemistry
• Computer Science
• Chromatography
• Atomic physics
• Computational biology
• Biology
• Database
• Materials science

Selected publications

• Preferential Formation and Stability of Copper Porphyrins amidst Other Metals in Dilute Aqueous Solution─Applications for Radiopharmaceuticals

  Inorganic Chemistry · 2026-02-23

  articleOpen accessSenior authorCorresponding

  Two worlds exist for cupration of a ligand: the preparative lab where natural-abundance copper (in pure form) is typically used in excess versus the ligand, and the radiochemistry lab where the ligand is in great excess versus the copper radionuclide (unavoidably accompanied by contaminating metal ions). Here, seven synthetic free base water-soluble porphyrins have been examined to assess molecular designs suitable for targeted radiotheranostics. Studies were carried out with equimolar quantities of a porphyrin and natural abundance (nonradioactive) CuCl2 (10–4–10–7 M) and other metals in aqueous HEPES buffer (1 M) at room temperature (detection by absorption and fluorescence spectroscopy). Studies also were carried out with 64CuCl2 and excess porphyrin at 37 °C. Key results are as follows: (1) competition experiments with CoCl2, NiCl2, CuCl2, ZnCl2, FeCl2, and FeCl3 gave selective cupration. (2) The copper chelates of the porphyrins were stable in the aqueous solution for at least 24 h. (3) Copper porphyrins were obtained in apparent molar activities (AMAs) ∼6000 mCi/μmol (222 GBq/μmol) even in the presence of other metals. The results augur well for use of copper chelates of designer porphyrins in radiomedicine.

  PublisherOA PDFDOI

• Digital Database of Absorption Spectra of Carotenoids Found in Food and Photosynthetic Organisms

  ACS Food Science & Technology · 2026-03-04

  articleOpen accessSenior authorCorresponding

  Carotenoids─ubiquitous pigments in the plant and animal kingdom─play roles in coloration, light-harvesting, photoprotection, and nutrition. More than 1200 carotenoids are known. The yellow, orange, or red color of carotenoids stems from absorption of light by the linear polyene chromophore. Here, a digital database of absorption spectra has been assembled for 44 naturally occurring carotenoids, which range from astaxanthin to zeaxanthin and encompass conjugation pathlengths from 7 (ζ-carotene) to 13 (spirilloxanthin) carbon–carbon double bonds. Three spectra are included for carotenoids that contain a central cis-configuration. The spectra encompass the often-neglected ultraviolet region (to 230 nm) and the well-known visible region (to 650 nm). An absorption spectrum of each carotenoid was recorded at room temperature in one or more solvents, and 27 carotenoids were examined at 77 K in frozen media. Altogether, 121 spectra were collected and have been made available in PhotochemCAD. The availability of curated digital spectra of diverse carotenoids enables comparison of structural effects and photophysical features, and should be particularly useful in studies of agriculture, ecology, nutrition, and photosynthesis.

  PublisherOA PDFDOI

• Synthesis and characterization of 5,15-bis(hydroxymethyl)porphyrins – simple compounds distantly inspired by the chlorosomal bacteriochlorophylls

  New Journal of Chemistry · 2026-01-01

  articleOpen accessSenior authorCorresponding

  Small changes in substituents of synthetic porphyrins profoundly alter the crystalline self-assembly patterns.

  PublisherOA PDFDOI

• Synthesis of bacteriochlorophyll <i>a</i>

  Chemical Science · 2026-01-01

  articleOpen accessSenior authorCorresponding

  . The modularity of the synthesis, straightforward construction of asymmetric building blocks, and convergent joining of AD and BC halves suggest that the present route may provide an entrée into diverse photosynthetic macrocycles.

  PublisherDOI

• Database of low‐temperature absorption and fluorescence spectra of native photosynthetic tetrapyrrole macrocycles

  Photochemistry and Photobiology · 2025-08-10 · 2 citations

  articleOpen accessSenior authorCorresponding

  Abstract Low‐temperature (77 K) absorption and fluorescence spectra of 12 naturally occurring photosynthetic tetrapyrrole macrocycles have been recorded in a frozen glass (2‐methyltetrahydrofuran). The compounds encompass distinct chromophore classes: porphyrin, chlorophyll c 2 ; chlorin, chlorophylls a , b , d , f and bacteriochlorophylls c , d , e , f ; and bacteriochlorin, bacteriochlorophylls a , b , g . The spectra are compared with those of the same pigment in liquid solution (predominantly 2‐methyltetrahydrofuran) at room temperature (293 K). The measured Stokes shifts at 77 K across the 12 macrocycles range from ~30 to 300 cm −1 . The spectral data in digital form are made available as part of the PhotochemCAD databases. Literature searches have revealed extensive published data for Chl a (often in biological matrices) but at best rather limited data for less common macrocycles. The availability of a systematic collection of curated spectral data collected at low temperature should be useful for a variety of assessments, including reconstruction of absorption spectra of (bacterio)chlorophyll‐containing protein complexes, vibrational analysis of absorption and fluorescence spectra, and calculations where knowledge of energy levels is important.

  PublisherOA PDFDOI

• Chatbots can guide measurement of absorption spectra with improved quality

  2025-01-23

  articleSenior author

  Absorption spectroscopy is a long-standing instrumental method for qualitative and quantitative analyses, yet is prone to errors given the richness of sample type, suite of instrumental limitations, and scope of possible human errors; hence, guidance for proper on-the-fly measurements is essential. Recent advances in transformer-based large language models have yielded conversational artificial intelligence (AI) chatbots. Here, the capabilities of six major chatbots (ChatGPT 4o, Gemini Advanced 1.5 Pro, Microsoft Copilot, Meta AI, Claude 3.5 Sonnet, and Grok 2) have been examined by requesting practical advice to achieve improved quality in the measurement of absorption spectra, where verbal descriptions were provided concerning the features of a poor-quality, experimentally collected spectrum already in hand. The suggestions by the chatbots were surprisingly on point in most cases. The results here imply a valuable role for chatbots in support of human analysts as well as automated experimental systems during the measurement of absorption spectra.

  PublisherDOI

• Single-crystal X-ray structure analysis of a synthetic chlorin

  Journal of Porphyrins and Phthalocyanines · 2025-02-01 · 1 citations

  articleSenior authorCorresponding

  Understanding the crystal-packing patterns of tetrapyrroles underpins a number of objectives in materials sciences. Here, the zinc chelate of 3,13-diacetyl-10-(pentafluorophenyl)-18,18-dimethylchlorin was prepared, crystallized in the presence of tetrahydrofuran (THF), and analyzed by single-crystal x-ray diffraction (SCXRD). The zinc chlorin (Zn1) afforded a herringbone pattern of parallel columnar stacks of chlorins rotated by 67.41[Formula: see text] with respect to each other. The chlorins within a column are stacked in pairs having interplanar distances of 3.289 Å within a pair and 4.407 Å between pairs. The chlorins in a pair are aligned in a “head-to-head” arrangement with cofacial [Formula: see text]–[Formula: see text] overlap chiefly only of the respective ring A units; the overall composition is thus of columnar stacks of slipped-stacked pairs of chlorins. Each chlorin is enantiomeric due to the coordination at the Zn(II) center of a single THF molecule; the juxtaposition of chlorin [Formula: see text]–[Formula: see text] faces opposite the apically ligated THF molecules affords a racemate. All chlorins in a column face in the same direction, with 3,13-acetyl groups essentially coplanar with the macrocycle and oriented toward the respective 5,15-positions (affording an O[Formula: see text]H–C contact of 2.33 or 2.39 Å), and with interdigitation of alternating pentafluorophenyl groups in adjacent columns. A large number of SCXRD analyses of synthetic chlorins will likely be required to understand the relationship between structure and assembly patterns.

  PublisherDOI

• Amino Acid Betaxanthins: Absorption, Fluorescence, And Stability

  Journal of Natural Products · 2025-06-20 · 1 citations

  articleOpen accessCorresponding

  . All spectral data have been made accessible in a PhotochemCAD absorption/fluorescence spectral database, enabling streamlined analysis and quantification.

  PublisherDOI

• Structural features of 11 synthetic bacteriochlorins — comparisons with chlorins and porphyrins

  Journal of Porphyrins and Phthalocyanines · 2025-09-01

  articleSenior author

  As part of a program to develop the fundamental science of synthetic bacteriochlorins — analogues of Nature’s light-harvesting pigments in anoxygenic photosynthesis — 11 synthetic free base bacteriochlorins have been examined by single-crystal X-ray diffraction analysis. In each bacteriochlorin, each pyrroline ring contains a gem-dimethyl group to block adventitious (aerobic) dehydrogenation. The structural features of the bacteriochlorins (tetrahydroporphyrins) are compared with the less saturated counterparts, chlorins (dihydroporphyrins) and porphyrins. Only slight structural perturbation accrues due to the presence of the gem-dimethyl groups. The results presented herein may aid in understanding metal chelation processes and underpin the development of functional solid-state molecular assemblies.

  PublisherDOI

• Studies of the amidation of porphyrin-NHS esters in dilute aqueous solution

  New Journal of Chemistry · 2025-01-01 · 2 citations

  articleOpen accessSenior authorCorresponding

  Quantitative kinetic studies of the dilute aqueous-solution reaction of porphyrin-NHS esters with a PEG-amine (2 equivalents) revealed conditions for amidation in high yield with only limited hydrolysis and byproduct formation.

  PublisherOA PDFDOI

Recent grants

• NIH Grant R01GM036238

  NIH · $4.4M · 2007

• Versatile Synthesis of Chlorophylls and Bacteriochlorophylls for Fundamental Studies in Photosynthesis

  NSF · $450k · 2018–2021

• A Chemical Model for the Prebiotic Origins of Tetrapyrrole Macrocycles

  NSF · $510k · 2010–2013

• Versatile Synthesis of Chlorophylls and Bacteriochlorophylls for Fundamental Studies in Photosynthesis

  NSF · $500k · 2021–2024

• A Chemical Model for the Prebiotic Origins of Tetrapyrrole Macrocycles

  NSF · $400k · 2013–2017

Frequent coauthors

• David F. Bocian

  University of California, Riverside

  530 shared

• Dewey Holten

  Washington University in St. Louis

  320 shared

• Masahiko Taniguchi

  Osaka University of Pharmaceutical Sciences

  204 shared

• James R. Diers

  University of California, Riverside

  190 shared

• Christine Kirmaier

  Washington University in St. Louis

  163 shared

• Robert S. Loewe

  North Carolina State University

  78 shared

• Richard W. Wagner

  The University of Texas MD Anderson Cancer Center

  69 shared

• Eve Hindin

  North Carolina State University

  63 shared

Labs

• Jonathan LindseyPI