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1. Solar energy driven C–C bond cleavage in a lignin model compound with a D–π–A organic dye-sensitized photoanode

   https://doi.org/10.1039/d3se00194f  

   Kim, Saerona ; Kang, Hyeong Cheol ; Chu, Chun ; Li, Shuya ; Yoo, Kicheon ; Wijethunga, Udani Kaushalya ; Zheng, Weiwei ; Yoo, Chang Geun ; Sherman, Benjamin D. ; Lee, Jae-Joon ; et al ( May 2023 , Sustainable Energy & Fuels)

   The high bond dissociation energy of C–C σ-bonds presents a challenge to chemical conversions in organic synthesis, polymer degradation, and biomass conversion that require chemoselective C–C bond cleavage at room temperature. Dye-sensitized photoelectrochemical cells (DSPECs) incorporating molecular organic dyes could offer a means of using renewable solar energy to drive these types of energetically demanding chemoselective C–C bond cleavage reactions. This study reports the solar light-driven activation of a bicyclic aminoxyl mediator to achieve C–C bond cleavage in the aryl-ether linkage of a lignin model compound (LMC) at room temperature using a donor–π-conjugated bridge–acceptor (D–π–A) organic dye-based DSPEC system. Mesoporous TiO 2 photoanode surfaces modified with 5-[4-(diphenylamino)phenyl]thiophene-2-cyanoacrylic acid (DPTC) D–π–A organic dye were investigated along with a bicyclic aminoxyl radical mediator (9-azabicyclo[3,3,1]nonan-3-one-9-oxyl, KABNO) in solution with and without the presence of LMC. Photophysical studies of DPTC with KABNO showed intermolecular energy/electron transfer under 1 sun illumination (100 mW cm −2 ). Under illumination, the D–π–A type DPTC sensitized TiO 2 photoanodes facilitate the generation of the reactive oxoammonium species KABNO+ as a strong oxidizing agent, which is required to drive the oxidative C–C bond cleavage of LMC. The photoelectrochemical oxidative reaction in a complete DSPEC with KABNO afforded C–C bond cleavage products 2-(2-methoxyphenoxy)acrylaldehyde (94%) and 2,6-dimethoxy-1,4-benzoquinone (66%). This process provides a first report utilizing a D–π–A type organic dye in combination with a bicyclic nitroxyl radical mediator for heterogeneous photoelectrolytic oxidative cleavage of C–C σ-bonds, modeled on those found in lignin, at room temperature. 

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2. Liquid–liquid equilibrium compositions and global phase behavior for the lignin–acetic acid–water system at 70 and 95 °C

   https://doi.org/10.1016/j.fluid.2018.01.002  

   Ding, Junhuan ; Klett, Adam S. ; Gamble, Jordan A. ; Tindall, Graham W. ; Thies, Mark C. ( April 2018 , Fluid Phase Equilibria)
3. Liquid–Liquid Equilibrium Compositions and Global Phase Behavior for Lignin–Acetone–Water Ternary at 25, 45, and 65 °C

   https://doi.org/10.1021/acs.iecr.9b03522  

   Temples, Spencer C. ; Gathmann, Sallye R. ; Ding, Junhuan ; Thies, Mark C. ( December 2019 , Industrial & Engineering Chemistry Research)
4. Permafrost Organic Carbon Mobilization From the Watershed to the Colville River Delta: Evidence From 14 C Ramped Pyrolysis and Lignin Biomarkers

   https://doi.org/10.1002/2017GL075543  

   Zhang, Xiaowen ; Bianchi, Thomas S. ; Cui, Xingqian ; Rosenheim, Brad E. ; Ping, Chien‐Lu ; Hanna, Andrea J. M. ; Kanevskiy, Mikhail ; Schreiner, Kathryn M. ; Allison, Mead A. ( November 2017 , Geophysical Research Letters)
5. Substrate Specificity of LACCASE8 Facilitates Polymerization of Caffeyl Alcohol for C-Lignin Biosynthesis in the Seed Coat of Cleome hassleriana

   https://doi.org/10.1105/tpc.20.00598  

   Wang, Xin ; Zhuo, Chunliu ; Xiao, Xirong ; Wang, Xiaoqiang ; Docampo-Palacios, Maite ; Chen, Fang ; Dixon, Richard A. ( October 2020 , The Plant Cell)