@article{tran_wang_matsumoto_liu_jing_nalaoh_nguyen_taniguchi_lindsey_2023, title={Bacteriochlorin syntheses - Status, problems, and exploration}, volume={8}, ISSN={["1099-1409"]}, url={https://doi.org/10.1142/S1088424623501171}, DOI={10.1142/S1088424623501171}, abstractNote={ Bacteriochlorins – Nature’s near-infrared (NIR) chromophores – are distinguished by an intense ([Formula: see text] ∼;105 M[Formula: see text]cm[Formula: see text] long-wavelength absorption band in the ∼;700–1000 nm. The development of routes to prepare synthetic, tailorable bacteriochlorins holds promise for multiple disciplines where NIR-light-promoted photoactivity is of interest. A de novo route to bacteriochlorins equipped with a stabilizing gem-dimethyl group in each pyrroline ring was discovered in 2003. Continued development in this arena over 20 years has led to additional routes as well as methods to install substituents at selected positions about the perimeter of the macrocycle. The present paper reports studies that highlight substantial limitations of existing synthetic routes, including stymied access to multi-bacteriochlorin arrays and the inability to install (in a rational way) distinct groups at opposite sides of the macrocycle. The origins of the limitations are traced to particular stages of the chemistry ranging from derivatizing pyrroles, creating pyrrolines, constructing and elaborating dihydrodipyrrins, coupling dihydrodipyrrins, and forming macrocycles. Through exploration of a dozen aspects of bacteriochlorin syntheses, 60 new compounds (and nine known compounds via improved syntheses) have been prepared and characterized; the data include 20 single-crystal X-ray diffraction analyses. The research taken together points to areas of focus to fulfill the promise of this fascinating class of compounds. }, journal={JOURNAL OF PORPHYRINS AND PHTHALOCYANINES}, author={Tran, Vy-Phuong and Wang, Pengzhi and Matsumoto, Nobuyuki and Liu, Sijia and Jing, Haoyu and Nalaoh, Phattananawee and Nguyen, Khiem Chau and Taniguchi, Masahiko and Lindsey, Jonathan S.}, year={2023}, month={Aug} } @article{takashima_inoue_matsumoto_takagi_okuda_2020, title={A fluorogenic probe using a catalytic reaction for the detection of trace intracellular zinc}, volume={56}, ISSN={["1364-548X"]}, DOI={10.1039/d0cc05315e}, abstractNote={A reaction-based fluorescent probe with cephem scaffold has been applied for signal amplification system to detect trace intracellular zinc.}, number={87}, journal={CHEMICAL COMMUNICATIONS}, author={Takashima, Ippei and Inoue, Yohei and Matsumoto, Nobuyuki and Takagi, Akira and Okuda, Kensuke}, year={2020}, month={Nov}, pages={13327–13330} } @article{matsumoto_taniguchi_lindsey_2020, title={Bioconjugatable synthetic chlorins rendered water-soluble with three PEG-12 groups via click chemistry}, volume={24}, ISSN={["1099-1409"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-85072584806&partnerID=MN8TOARS}, DOI={10.1142/S1088424619501219}, abstractNote={ Chlorins provide many ideal features for use as red-region fluorophores but require molecular tailoring for solubilization in aqueous solution. A chlorin building-block bearing 18,18-dimethyl, 15-bromo and 10-[2,4,6-tris(propargyloxy)phenyl] substituents has been transformed via click chemistry with CH3(OCH2CH[Formula: see text]-N3 followed by Suzuki coupling with 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid, thereby installing a water-solubilization motif and a bioconjugatable handle, respectively. In toluene, [Formula: see text]-dimethylformamide (DMF) or water, the resulting facially encumbered free base chlorin exhibits characteristic chlorin absorption ([Formula: see text] [Formula: see text]412, 643 nm) and fluorescence ([Formula: see text] [Formula: see text]645 nm) spectra with only modest variation in fluorescence quantum yield ([Formula: see text] values (0.24, 0.25 and 0.19, respectively). The zinc chlorin derived therefrom exhibits similar spectral constancy ([Formula: see text] [Formula: see text]414 and 613 nm, [Formula: see text] [Formula: see text]616 nm) and [Formula: see text] 0.094, 0.10 and 0.086 in the three solvents. The results together indicate the viability of the molecular design and synthetic methodology to create red-region fluorophores for use in diverse applications. }, number={1-3}, journal={JOURNAL OF PORPHYRINS AND PHTHALOCYANINES}, author={Matsumoto, Nobuyuki and Taniguchi, Masahiko and Lindsey, Jonathan S.}, year={2020}, pages={362–378} } @article{zhang_wu_takashima_nguyen_matsumoto_lindsey_2020, title={Engineering of an archaeal phosphodiesterase to trigger aggregation-induced emission (AIE) of synthetic substrates}, volume={44}, ISSN={["1369-9261"]}, DOI={10.1039/d0nj03208e}, abstractNote={Aggregation-induced emission (AIE) probes that can be triggered by enzymatic activity are valuable for applications across the life sciences.}, number={33}, journal={NEW JOURNAL OF CHEMISTRY}, author={Zhang, Yunlong and Wu, Zhiyuan and Takashima, Ippei and Nguyen, Kathy-Uyen and Matsumoto, Nobuyuki and Lindsey, Jonathan S.}, year={2020}, month={Sep}, pages={14266–14277} } @article{fujita_dou_matsumoto_wu_lindsey_2020, title={Enzymatically triggered chromogenic cross-linking agents under physiological conditions}, volume={44}, ISSN={["1369-9261"]}, DOI={10.1039/c9nj04126e}, abstractNote={Oxidative dimerization of an indoxyl moiety, released by glycosidase action in aqueous solution, yields an indigoid dye in formats that enable bioconjugation and molecular cross-linking.}, number={3}, journal={NEW JOURNAL OF CHEMISTRY}, author={Fujita, Hikaru and Dou, Jinghuai and Matsumoto, Nobuyuki and Wu, Zhiyuan and Lindsey, Jonathan S.}, year={2020}, month={Jan}, pages={719–743} }