Article
Chemistry, Organic
Samrat Kundu, Lisa Roy, Modhu Sudan Maji
Summary: In this study, a unique carbazole-based organophotocatalyst, benzoperylenocarbazole (BPC), is reported as a potent organo-photoreductant. BPC exhibits a lower excited state oxidation potential and a reasonable excited state lifetime, making it an effective photosensitizer. With low catalyst loading and irradiation of blue light, a variety of vicinal diols and diamines can be synthesized in excellent yields through reductive coupling of carbonyls and imines. DFT calculations provide insight into the electronic structure of BPC.
Article
Chemistry, Multidisciplinary
Francesco Calogero, Simone Potenti, Elena Bassan, Andrea Fermi, Andrea Gualandi, Jacopo Monaldi, Busra Dereli, Bholanath Maity, Luigi Cavallo, Paola Ceroni, Pier Giorgio Cozzi
Summary: In this study, a highly enantioselective photoredox allylation of aldehydes was developed using commercially available allyl acetate and chiral nickel complexes as the catalyst. The reaction proceeded under visible-light irradiation at low temperature, providing good to excellent yields and high enantioselectivity. This methodology shows great potential for practical applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Luigi Dolcini, Tommaso Gandini, Riccardo Castiglioni, Alberto Bossi, Marta Penconi, Alberto Dal Corso, Cesare Gennari, Luca Pignataro
Summary: This study investigates the use of organic photocatalysts for visible light-promoted beta-functionalization of carbonyl compounds. Donor-acceptor cyanoarenes showed the best results among the tested dyes, promoting the desired transformations in moderate to good yields. The reaction scope was explored on substrates with different steric and electronic properties, and a reductive quenching mechanism involving a transient 5 pi e(-) activation mode was proposed based on fluorescence quenching analysis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Pan Pan, Shihan Liu, Yu Lan, Huiying Zeng, Chao-Jun Li
Summary: A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. Hydrazones were used as alternatives to organometallic reagents, making this cross-coupling mild and green. Mechanistic investigations revealed the formation of an electron donor-acceptor complex, generating an aryl radical via single-electron transfer.
Article
Chemistry, Organic
Feng Chen, Xiu-Hua Xu, Lingling Chu, Feng-Ling Qing
Summary: A photochemically induced, nickel-catalyzed radical cross-coupling reaction has been developed for the synthesis of alpha-aryl-alpha-trifluoromethyl alcohols. This reaction utilizes a photoinduced charge transfer process between Hantzsch ester and phthalimido trifluoroethanol to generate a radical intermediate for the cross-coupling with aryl bromides. The protocol is mild and operationally simple, without the need for exogenous photocatalysts or stoichiometric metal reductants, and exhibits broad substrate compatibility and excellent functional group tolerance.
Article
Polymer Science
Busra Nakipoglu, Cansu Aydogan, Mucahit Ozdemir, Yusuf Yagci, Sermet Koyuncu, Baris Kiskan
Summary: This study presents a simple and efficient method for synthesizing conjugated poly(phenylene butadiynylene) (PPB) polymers using photo-induced radical homocoupling. The resulting PPB polymers exhibited a red shift in the optical properties and a decrease in the band gap and oxidation potential. Transmission electron microscopy and atomic force microscopy measurements revealed the self-organization of the PPB polymers into planar 2D nanorods, supported by density functional theory calculations. The surface area of the polymer was determined to be 53.61 and 30.69 m(2)/g using Brunauer-Emmett-Teller and Barrett-Joyner-Halenda methods, respectively.
Article
Chemistry, Applied
Yu Gao, Sara Sparascio, Lorenzo Di Terlizzi, Massimo Serra, Guanglu Yue, Yaru Lu, Maurizio Fagnoni, Xia Zhao, Stefano Protti
Summary: Two visible-light mediated protocols for the synthesis of aryl thiocyanates and aryl selenocyanates from arylazo sulfones are presented. The reactions make use of the unique photoreactivity and redox activity of the substrates, and exhibit high yields and wide scope.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Feng Lan, Cheng-Song Liu, Cen Zhou, Xiaozhou Huang, Jun-Yan Wu, Xiao Zhang
Summary: This study designed an organic polymer photocatalyst TX-OXD-P, which can catalyze organic transformations in a metal-free and recyclable manner. It exhibits strong reducing power and enhanced visible-light absorption, providing new insights into the exploration of novel photocatalytic performance of organic polymers.
JOURNAL OF MATERIALS CHEMISTRY A
(2022)
Article
Chemistry, Physical
Martijn Peters, Derese Desta, Senne Seneca, Gunter Reekmans, Peter Adriaensens, Jean-Paul Noben, Niels Hellings, Tanja Junkers, Anitha Ethirajan
Summary: Conjugated polymer nanoparticles (CNPs) are highly valued in bioimaging for their optical properties and biocompatibility, but face issues with unspecific protein adsorption. Research shows that PEGylation can modulate the uptake of CNPs by brain cells without affecting their optical properties, highlighting their potential as excellent bioimaging tools.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2021)
Article
Chemistry, Multidisciplinary
Yunhui Feng, Hang Luo, Fangnian Yu, Qian Liao, Luqing Lin
Summary: Here, we present a visible-light-promoted single nickel catalysis for achieving various C-N couplings of aryl chlorides/bromides and diverse N-nucleophiles using sodium iodide as the activator. The single nickel catalyst plays a dual role in halogen exchange and C-N coupling, which are crucial for obtaining the desired coupling products. This catalytic process eliminates the need for an exogenous photocatalyst and offers a sustainable and efficient approach for mild C-N coupling. Experimental studies, along with UV-vis and NMR analyses, demonstrate that the halogen exchange between both Ni-II and Ni-III-halide complexes and the iodide anion is a significant process in the formation of coupling products.
Article
Chemistry, Physical
Tammy X. Leong, Layla N. Qasim, Robert T. Mackin, Yuchen Du, Robert A. Pascal, Igor V. Rubtsov
Summary: A method of rapidly and unidirectionally funneling high-frequency vibrational quanta over large distances using oligo(p-phenylene) chains has been discovered. The transport of high-energy vibrational quanta with speeds reaching 8.6 km/s can be controlled by tuning the degree of conjugation via electronic doping of the chain, opening avenues for developing materials with controllable energy transport properties for heat management and initiating chemical reactions remotely.
JOURNAL OF CHEMICAL PHYSICS
(2021)
Article
Chemistry, Multidisciplinary
Naoyuki Toriumi, Tomonori Inoue, Nobuharu Iwasawa
Summary: This study reports the design of a photosensitizing ligand for single transition-metal catalysis under visible-light irradiation, which has been successfully applied to the cross-coupling reaction of aryl halides with carboxylic acids. The ligand allows the use of different aryl halides and light wavelengths for the reaction. Experimental and theoretical studies reveal that photoinduced electron transfer promotes the reductive elimination reaction in the excited state.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Zi-Wei Xi, Lei Yang, Dan-Yan Wang, Chuan-Wei Feng, Yufeng Qin, Yong-Miao Shen, Chaodan Pu, Xiaogang Peng
Summary: An efficient visible light-driven methodology using CdSe/CdS core/shell quantum dots as photocatalysts selectively transforms aryl aldehydes and ketones to alcohols or pinacol products, with thiophenols acting as donors and hole traps. The catalysts show high efficiency and stability, with the ability to switch products simply by adjusting the amount of thiophenol. The method allows for good functional group tolerance, mild reaction conditions, and is suitable for large scale reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Yurachat Janpatompong, Kamil Suwada, Michael L. Turner, Guillaume De Bo
Summary: Understanding the stability of conjugated polymers towards mechanical stimuli is crucial for optimizing their use in electronic and optoelectronic devices. Mechanochemistry is a field that aims to control mechanical forces for chemical changes, and it can also be used to study the stability of conjugated polymers. Ultrasonication is a technique that can be used to test the mechanical integrity of phenylenevinylene block copolymers and demonstrate their stability to mechanical forces, making them suitable for flexible organic electronics.
Review
Energy & Fuels
Zhuangfei Qian, Kai A. I. Zhang
Summary: Conjugated microporous polymers (CMPs), as metal-free, pure organic and heterogeneous photocatalysts, have attracted attention due to their organic nature, ease of synthesis, structural diversity, and low costs. Researchers focus on crucial factors affecting the catalytic performance of CMPs, such as band structure, charge transfer, morphology, as well as specific applications like water splitting, CO2 reduction, and organic photoredox reactions.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
