Article
Nanoscience & Nanotechnology
Pengcheng Miao, Ziyue Jiao, Jie Liu, Maomao He, Guanjun Song, Zhiyong Wei, Xuefei Leng, Yang Li
Summary: In this study, a new kind of shape memory polyhydroxyurethane (PHU) material with outstanding mechanical properties and chemical recyclability is prepared through the aminolysis reaction of cyclic carbonate. The synthetic strategy, which is isocyanate-free and uses CO2 as a building block, is environmentally friendly and aligns with the concept of carbon neutrality. The thermal properties, mechanical properties, and dynamic behaviors of the PHUs are investigated, showing superior performance compared to other reported PHU-based materials.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Organic
Cedric L. Hugelshofer, Jianming Bao, Juana Du, Eric Ashley, Wensheng Yu, Tao Ji, Bin Hu, Dejun Liu, Ramu Rondla, Srinivas Karampuri, Vishal Sharma, Krishna Ethiraj, Yeon-Hee Lim
Summary: This article provides details of a synthetic strategy for the efficient preparation of an important cyclic sulfone compound for medicinal chemistry. A practical and scalable protocol has been developed to easily access the target compound from commercially available and inexpensive starting materials, enabling the synthesis of various related derivatives.
Article
Polymer Science
Guilhem Coste, Dimitri Berne, Vincent Ladmiral, Claire Negrell, Sylvain Caillol
Summary: Polyurethane foams, currently dominating the global foam market, face the challenge of using toxic isocyanate reagents. A new tetrafunctional cyclic carbonate, TC6, has been synthesized, leading to the successful production of polyhydroxyurethane (PHU) foams. These PHU foams exhibit interesting properties and have the potential to be used in applications such as seating or insulation mattresses.
EUROPEAN POLYMER JOURNAL
(2022)
Article
Chemistry, Organic
Seo-Jung Han, Marchello A. Cavitt, Brian M. Stoltz
Summary: An efficient method for the direct synthesis of eight-membered nitrogen-containing heterocycles from secondary and tertiary alcohols was developed. This operationally simple reaction tolerates various functional groups and is applicable to the synthesis of diverse medium-sized ring nitrogen-containing heterocycles.
Article
Chemistry, Organic
Wanshu Wang, Lu Gao, Zhenlei Song
Summary: This article reviews the recent advances in the synthesis of silaazacycles, including different types and moieties of five- and six-membered silaazacycles. These advances are of great significance for the development of silicon-containing functional molecules.
SYNTHESIS-STUTTGART
(2022)
Article
Polymer Science
Jie Liu, Pengcheng Miao, Xuefei Leng, Jian Che, Zhiyong Wei, Yang Li
Summary: In this study, non-isocyanate polyurethanes (NIPUs) were synthesized from renewable bis(6-membered cyclic carbonates) and amines. The resulting NIPUs exhibited excellent mechanical properties and thermal stability. They could be remolded and chemically degraded into bi(1,3-diol) precursors, which could then be used to regenerate NIPUs with similar structures and properties. This synthetic strategy, which is isocyanate-free and utilizes isoeugenol and carbon dioxide as building blocks, offers an attractive pathway to NIPU networks and contributes to achieving a circular economy.
MACROMOLECULAR RAPID COMMUNICATIONS
(2023)
Review
Polymer Science
Zaher Abdel Baki, Hanna Dib, Tuba Sahin
Summary: This review focuses on the synthesis of polycarbonate via ring-opening polymerization of cyclic carbonates. It discusses various initiating systems and their mechanisms, as well as the challenges in preparing the polymers and controlling their properties. It highlights the importance of glycerol carbonate as a CO2 fixation agent and its potential as an alternative to Bisphenol A in polycarbonate synthesis.
Review
Biochemistry & Molecular Biology
Rida Noor, Ameer Fawad Zahoor, Asim Mansha, Samreen Gul Khan, Atta Ul Haq, Sajjad Ahmad, Sami A. Al-Hussain, Ali Irfan, Magdi E. A. Zaki
Summary: Ring expansion reactions have attracted synthetic chemists due to their significance in synthesizing biologically active compounds and their effectiveness in medicinal chemistry. This review provides an overview of various synthetic methodologies employed by scientists for constructing medium- to large-size carbo- and heterocycles including lactams, lactones, azepines, and azulene derivatives via the ring expansion of six-membered carbo- and heterocycles. The literature from 2007 to 2022 is covered, with numerous rearrangement and cycloaddition reactions such as Tiffeneau-Demjanov rearrangement, Aza-Claisen rearrangement, Schmidt rearrangement, and Beckmann rearrangement being discussed.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Review
Biochemistry & Molecular Biology
Kashaf Babar, Ameer Fawad Zahoor, Sajjad Ahmad, Rabia Akhtar
Summary: The synthesis of spirocyclic compounds has garnered attention from synthetic chemists for their privileged ring system and efficacy in drug discovery. Many natural compounds with spirocyclic moieties are effective in the pharmaceutical industry. Recent synthetic methodologies have been established for constructing various spirocompounds containing six-membered carbocycles/heterocycles.
MOLECULAR DIVERSITY
(2021)
Review
Chemistry, Medicinal
Naiera M. Helmy, Keykavous Parang
Summary: Fungal infections pose a significant threat to human health, and there is a growing interest in antifungal research due to microbial resistance, improper use of antimicrobial drugs, and the need for less toxic treatments. Cyclic peptides, specifically antifungal peptides, have been studied as potential agents since 1948. Recent years have seen increased attention to exploring cyclic peptides as a promising strategy in combating antifungal infections caused by pathogenic fungi. This review highlights antifungal cyclic peptides isolated from various sources, emphasizing the need for further exploration of their therapeutic applications.
Article
Polymer Science
Takenori Nishida, Kotaro Satoh, Masazumi Tamura, Yingai Li, Keiichi Tomishige, Masami Kamigaito
Summary: This work is a comprehensive study of the cationic and radical polymerizations of exo-methylene six-membered conjugated dienes, investigating the effects of substituents on monomer reactivities and thermal properties of the polymers. The results show that the position of the methyl group and the isopropyl substituents play important roles in the monomer reactivity, and the unique structures of the biobased compounds enhance the thermal properties of the resulting polymers.
Article
Chemistry, Physical
Sonia Zeba Hashmi, Jaya Dharma, Dharma Kishore, Aleksey E. Kuznetsov
Summary: The present study reports the synthesis, NMR study, and computational investigation of novel s-triazine analogues embellished with bioactive heterocyclic scaffolds. The synthesis of these compounds was performed by exploiting the synthetic potential of a chalcone derived from s-triazine bound aryl ketone. Detailed DFT study corroborated the experimental findings and suggested possible noncovalent interactions between the molecules of these compounds. The global reactivity parameters analysis indicated the stability of these compounds in redox processes.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Vinh Do Cao, Dong Geun Jo, Huiae Kim, Changeun Kim, Seula Yun, Seewon Joung
Summary: A convenient strategy for synthesizing six-membered cyclic amidines from isoquinolines and pyridines has been developed in this study, using borane-catalyzed hydrosilylation as a dearomatizing tool. The broad substrate scope allows for various reaction pathways depending on the substitution pattern of the N-heteroarenes, resulting in rarely reported (Z)-sulfonyl amidine products that are mostly unprecedented. The scalability of this method and versatility of the cyclic amidine products are also highlighted.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Zheng-Feng Zhang, Ming-Der Su
Summary: Three fundamental concepts (aromaticity/basicity/electrophilicity) have been applied to study the chemical reactivity of six-membered-ring group 13 N-heterocyclic carbenes using density functional theory. The reactivity of different group 13 elements in the N-heterocyclic carbenes is determined by their HOMO or LUMO, with smaller atomic radius elements exhibiting higher aromaticity. Theoretical findings suggest that lower atomic number and smaller atomic radius of the group 13 atom result in easier chemical reactions in the N-heterocyclic carbene analogues.
Article
Chemistry, Inorganic & Nuclear
M. Carmen de la Fuente, Lucia Ageitos, Marta A. Lages, Diana Martinez-Matamoros, Abel M. Forero, Miguel Balado, Manuel L. Lemos, Jaime Rodriguez, Carlos Jimenez
Summary: This study successfully performed stereo-selective total synthesis of Pcb analogues, which are siderophores produced by pathogenic Gram-negative bacteria. The replacement of the acid-sensitive α-methylthiazoline moiety with a more stable thiazole ring and varying the OH group configuration at C-13 resulted in different metal coordination abilities. The study also confirmed the stereochemistry of the Ga3+ complex and proposed the scaffold's potential use in designing new chelating agents or antibacterials.
INORGANIC CHEMISTRY
(2023)
Article
Biochemical Research Methods
Mahmoud Elsabahy, Karen L. Wooley, Amy Hendricksen, Kenneth Oh
Summary: A robust data mining algorithm is presented as a critical solution to managing data from multiplexing techniques, allowing simultaneous detection of multiple biomarkers in a single sample. This algorithm has been successfully applied as a diagnostic and therapeutic monitoring tool in managing breast cancer.
Article
Multidisciplinary Sciences
Tan P. Nguyen, Alexandra D. Easley, Nari Kang, Sarosh Khan, Soon-Mi Lim, Yohannes H. Rezenom, Shaoyang Wang, David K. Tran, Jingwei Fan, Rachel A. Letteri, Xun He, Lu Su, Cheng-Han Yu, Jodie L. Lutkenhaus, Karen L. Wooley
Summary: The rapid development of lithium-ion batteries has brought substantial benefits to society, but also highlighted ethical and environmental challenges. Organic redox-active materials may offer a potential alternative for sustainable batteries in the future.
Article
Chemistry, Multidisciplinary
Nari Kang, Sangho Cho, Eric E. Leonhardt, Chun Liu, Stanislav V. Verkhoturov, William Henry Hunter Woodward, Michael J. Eller, Tianyu Yuan, Thomas C. Fitzgibbons, Yannick P. Borguet, Ashlee A. Jahnke, Anatoliy N. Sokolov, Travis McIntire, Carl Reinhardt, Lei Fang, Emile A. Schweikert, Liam Patrick Spencer, Guorong Sun, Guohua Xie, Peter Trefonas, Karen L. Wooley
Summary: By constructing brush-like polymers, the vertical alignment of polymer side chains in thin films was achieved, leading to an improvement in the efficiency of organic light-emitting diodes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Pharmacology & Pharmacy
Juanjuan Yang, Xiaojin Wang, Bingshun Wang, Kinam Park, Karen Wooley, Shiyi Zhang
Summary: Nanomedicines for cancer treatment have been extensively studied, but only a few have been approved by the FDA. The mismatch between effort and return raises questions about the field's understanding. The concept of tumor-targeted drug delivery has been based on assumptions that increased drug delivery to tumors improves efficacy and decreased delivery to healthy organs reduces side effects. However, clinical evidence shows that the maximum drug delivery limit to solid tumors has already been reached in humans, yet the efficacy and safety remain unchanged. The approvals of nanomedicine formulations were mostly based on changes in dose-limiting toxicity rather than improved tumor delivery.
ADVANCED DRUG DELIVERY REVIEWS
(2022)
Article
Pharmacology & Pharmacy
Lu Su, Kellie S. Dalby, Hannah Luehmann, Sussana A. Elkassih, Sangho Cho, Xun He, Lisa Detering, Yen -Nan Lin, Nari Kang, Dennis A. Moore, Richard Laforest, Guorong Sun, Yongjian Liu, Karen L. Wooley
Summary: A facile strategy to prepare ultrasmall nanoparticulate X-ray contrast media has been established for noninvasive clinical and preclinical cancer imaging. The synthesized amphiphilic statistical iodocopolymers can dissolve in water to form stable solutions with high aqueous iodine concentrations. In a breast cancer mouse model, the iodinated nano-XRCM showed extended blood residency and higher tumor accumulation, allowing for longitudinal monitoring of tumor retention for imaging or potential therapeutic effect.
ACTA PHARMACEUTICA SINICA B
(2023)
Review
Biotechnology & Applied Microbiology
Fatma Al-Zahraa Sayed, Noura G. Eissa, Yidan Shen, David A. Hunstad, Karen L. Wooley, Mahmoud Elsabahy
Summary: The morphology design of nanoparticles plays a crucial role in optimizing antimicrobial activity, considering factors such as bacteria shape, invasion mechanisms, and interactions with host cells. Some studies suggest spherical shapes exhibit improved antimicrobial activity compared to non-spherical structures, while others report higher activity for non-spherical forms (e.g., rod, discoid).
JOURNAL OF NANOBIOTECHNOLOGY
(2022)
Article
Polymer Science
Ching Pang, Hai Wang, Fuwu Zhang, Ami K. Patel, Hung Pang Lee, Karen L. Wooley
Summary: A series of glucose-based degradable superabsorbent hydrogels have been designed and fabricated to address issues related to sustainability, flooding, and drought. These hydrogels were constructed by integrating glucose into cyclic oligomers and block polymers, which were further combined into mechanically-interlocked slide-ring crosslinked materials. The optimized hydrogels exhibited water uptake capacities >30 times their own mass and were derived from renewable natural products, showing potential for high-performance applications.
JOURNAL OF POLYMER SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Yidan Shen, Mingwan Leng, Yunchong Yang, Senthil Kumar Boopathi, Guorong Sun, Karen L. Wooley
Summary: The substituents on the five-membered bicyclic glucose carbonate monomers have significant effects on the reactivity and regioselectivity during ring-opening polymerization. The thermal properties of the resulting polycarbonates are also influenced by these substituents.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Justin A. Smolen, Karen L. Wooley
Summary: This study demonstrates that convolutional neural networks can achieve high accuracy in cell detection and classification when applied to histology images acquired by FLIM, without the need for large amounts of data. The generated FLIM images show high similarity to ground truth images, leading to improved accuracy in cell detection and classification.
Article
Polymer Science
Maninderjeet Singh, Mei Dong, Wenjie Wu, Roushanak Nejat, David K. Tran, Nihar Pradhan, Dharmaraj Raghavan, Jack F. Douglas, Karen L. Wooley, Alamgir Karim
Summary: The maximum capacitive energy stored in polymeric dielectric capacitors is limited by the dielectric breakdown strength of the dielectric polymer. However, cyclic polymers have higher dielectric breakdown strength and capacitive energy density compared to linear polymers. Additionally, cyclic polymers exhibit a higher packing density.
Article
Polymer Science
Maninderjeet Singh, Mei Dong, Wenjie Wu, Roushanak Nejat, David K. Tran, Nihar Pradhan, Dharmaraj Raghavan, Jack F. Douglas, Karen L. Wooley, Alamgir Karim
Summary: The maximum capacitive energy stored in polymeric dielectric capacitors is determined by the dielectric breakdown strength of the dielectric polymer. The mechanisms of dielectric breakdown are not clear, but it was found that cyclic polymers exhibit enhanced stability in comparison to linear polymers, resulting in increased dielectric breakdown strength and capacitive energy density. Furthermore, cyclic polymers have a denser packing density than linear polymers.
Review
Chemistry, Multidisciplinary
Rana A. Eissa, Hesham A. Saafan, Aliaa E. Ali, Kamilia M. Ibrahim, Noura G. Eissa, Mostafa A. Hamad, Ching Pang, Hongming Guo, Hui Gao, Mahmoud Elsabahy, Karen L. Wooley
Summary: This tutorial review discusses recent advances in the synthesis and fabrication of degradable hemostatic nanomaterials and nanocomposites. The development of degradable smart devices and scaffolds has enabled efficient control of bleeding and gradual degradation.
Article
Materials Science, Multidisciplinary
Zhiming Liang, Tan P. Nguyen, N. Harsha Attanayake, Alexandra D. Easley, Jodie L. Lutkenhaus, Karen L. Wooley, Susan A. Odom
Summary: Non-aqueous organic redox flow batteries (NAORFBs) are emerging large-scale energy storage systems with a larger voltage window and metal-free nature. However, low solubility, sustainability, and crossover of redox materials are major challenges. In this study, redox active alpha-helical polypeptides suitable for NAORFBs are used, which demonstrate less crossover than small molecule analogs and exhibit low capacity fade and high coulombic efficiency. The polypeptides offer naturally-derived, deconstructable platforms for metal-free energy storage.
MATERIALS ADVANCES
(2022)
Article
Chemistry, Multidisciplinary
Yidan Shen, Xin Yang, Yue Song, David K. Tran, Hai Wang, Jaye Wilson, Mei Dong, Mariela Vazquez, Guorong Sun, Karen L. Wooley
Summary: Rigorous investigations of organobase-catalyzed ring-opening polymerizations (ROPs) of cyclic carbonate monomers derived from glucose revealed the scrambling of polycarbonate backbones due to competing transcarbonylation reactions. Experimental and computational studies provided insights into the regiochemistry resulting from the ring-opening and transcarbonylation reactions, which can guide the design and development of advanced carbohydrate-derived polymer materials.
Article
Polymer Science
David K. Tran, Ahmed Z. Rashad, Donald J. Darensbourg, Karen L. Wooley
Summary: The synthetic transformation of d-xylose into a four-membered cyclic ether enables reactions with carbon dioxide to produce linear polycarbonates through either one-step ring-opening copolymerisation (ROCOP) directly or sequential isolation of a preformed six-membered cyclic carbonate followed by ring-opening polymerisation (ROP).