Article
Chemistry, Organic
Jian-Bin Lu, Shu-Yuan Liang, Wu-Tao Gui, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A relay catalytic protocol utilizing pyrrolidine and palladium catalysis has been developed for the asymmetric synthesis of 1,3-diamine derivatives from 3-substituted 1,3-dienes, sulfuric diamide, and aldehydes. This one-pot, three-component reaction offers the advantages of high atom step economy and operational simplicity, providing an efficient and straightforward access to valuable 1,3-diamines containing quaternary and tertiary stereogenic centers with moderate to good enantioselectivity.
Article
Chemistry, Organic
Xiaofeng Zhang, Xiaoming Ma, Wei Zhang
Summary: This article highlights recent work on the development of alpha-amino acid-based [3 + 2] cycloaddition reactions of N-H-type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Keita Tanaka, Martin-Louis Y. Riu, Brian Valladares, Christopher C. Cummins
Summary: In this study, a new class of Azophosphines and N-heterocyclic iminophosphoranes (NHIPs) were successfully synthesized. The NHIPs exhibited tunability of steric demands and good basicity. The facile and scalable synthesis of NHIPs suggests their potential applications in synthetic chemistry.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Keita Tanaka, Martin-Louis Y. Riu, Brian Valladares, Christopher C. Cummins
Summary: This study presents the preparation and cycloaddition reactions of Azophosphines. The results show that these compounds have good adaptability to phosphorus atom substituents and can generate structures similar to cyclic (alkyl)(amino)carbenes. The NHIPs exhibit strong sigma-donor strengths and basicity, and display unique reactivity in certain reactions. The tunability of steric demands and scalability of these compounds suggest that they may have a wide range of applications in synthetic chemistry.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhenni Zhao, Zhi Ou, Subarna Jyoti Kalita, Feng Cheng, Qian Huang, Yangyi Gu, Yuhao Wang, Yan Zhao, Yiyong Huang
Summary: This paper reports the first example of a stereoconvergent reaction involving 1,3-dipolar cycloaddition of nitrile oxides and nitrile imines with electron-deficient olefins. The reaction produces compounds with multiple stereogenic centers and exhibits excellent regio- and diastereoselectivities. Through control experiments and calculations, the possibility of thermodynamically stable diastereomers formation during the reaction is ruled out, and a stepwise mechanism is proposed.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Houda Gazzeh, Fadwa Rouatbi, Sami Chniti, Moheddine Askri, Michael Knorr, Carsten Strohmann, Christopher Golz, Al Mokhtar Lamsabhi
Summary: The mechanism of a three-component one-pot cycloaddition reaction was studied using both theoretical and experimental methods. The reactivity difference between the unsymmetrical exocyclic dienones was analyzed to explain the observed regio- and stereoselectivity, and the results were confirmed by calculations. The reaction proceeded under kinetic control and showed chemoselectivity, producing two highly diastereomerically enriched compounds. The intermolecular hydrogen bonding and optical properties of the products were also investigated.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Dennis Svatunek, Thomas Hansen, Kendall N. Houk, Trevor A. Hamlin
Summary: The Lewis base F- catalyzes the 1,3-dipolar cycloaddition between CO2 and nitrilimines by activating the nitrilimine and enhancing the rate of the reaction. The strength of primary orbital interactions between the reactants is the origin of this catalysis. The Lewis base activated nitrilimine-F- has high-lying filled FMOs, which promote a rapid nucleophilic attack and overall cycloaddition with CO2.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sha Li, Yahan Sun, Xiaofang Li, Oskar Smaga, Sebastian Koniarz, Marcin Stepien, Piotr J. Chmielewski
Summary: A 1,3-cycloaddition reaction between 2-(tert-butyl)-8H-isoquinolino[4,3,2-de]phenanthridin-9-ium chloride and Ni-II norcorrole in the presence of base has been demonstrated to yield a family of chiral derivatives fused with pyrrole subunits of the macrocycle. Dehydrogenation of the cycloaddition products leads to dibenzoullazine ortho-fused antiaromatic porphyrinoids.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Analytical
Maryam Mehrdadian, Sadegh Khazalpour, Ameneh Amani
Summary: The electrochemical reaction of 4-ethynylaniline with sodium azide in buffered solutions at different pH values was investigated for the first time. A triazole ring was successfully synthesized through a series of electrochemical oxidations and chemical reactions, using a non-catalytic procedure at room temperature.
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
(2022)
Article
Chemistry, Physical
Ali Oubella, Yassine Laamari, Mouhi Eddine Hachim, Said Byadi, Aziz Auhmani, Hamid Morjani, Abdelkhalek Riahi, Crtomir Podlipnik, Taoufik Rohand, Luc Van Meervelt, My Youssef Ait Itto
Summary: A series of gem-dichlorocyclopropane-pyrazole hybrids were synthesized and their structure and anticancer activity were investigated. The synthesized compounds exhibited interesting antiproliferative activities.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Multidisciplinary
Mohammed F. F. Radwan, Elghareeb E. E. Elboray, Hemat M. M. Dardeer, Yusuke Kobayashi, Takumi Furuta, Shohei Hamada, Toshifumi Dohi, Moustafa F. F. Aly
Summary: 1,3-Dipolar cycloaddition through in situ generation of azomethine ylide provides a straightforward and critically important sustainable approach for access to diverse pyrrolidine chemical space. Metal-free AcOH-activated 1,3-dipolar cycloaddition protocol was developed to synthesize uncommon pyrrolidine cycloadducts with excellent diastereoselectivity. The reaction mechanism and the key role of AcOH were supported by experimental, theoretical and spectroscopic studies.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Dmitriy D. Karcev, Mariia M. Efremova, Alexander P. Molchanov, Nikolai Rostovskii, Mariya A. Kryukova, Alexander S. Bunev, Dmitry A. Khochenkov
Summary: In this study, new highly functionalized 5-spiroisoxazolidines were synthesized through the 1,3-dipolar cycloaddition reaction, which showed good selectivity. The reversibility of these reactions allows for controlling the diastereoselectivity of cycloaddition. Additionally, the reduction reaction of the obtained adducts provides 1,3-aminoalcohols or spirolactones.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Guipeng Feng, Guoyang Ma, Wenyan Chen, Shaohong Xu, Kaikai Wang, Shaoyan Wang
Summary: The [3 + 2] 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved, resulting in a range of tetrahydroisoquinoline derivatives with good diastereoselectivities and enantioselectivities. The absolute configuration of the product was determined using quantum electronic circular dichroism calculation and ECD spectrum method.
Article
Chemistry, Organic
Chaima Messaoudi, Momtez Jmai, Badr Jismy, Mohamed Abarbri, Hedi M'rabet
Summary: An efficient and original method for the synthesis of aminophosphonate-containing isoxazoline derivatives is described. A library of various substituted compounds can be readily synthesized through a 1,3-dipolar cycloaddition reaction under mild conditions.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Kan-Lei Ji, Shu-Fan He, Dong-Dong Xu, Wen-Xin He, Jian-Feng Zheng, Pei-Qiang Huang
Summary: A concise asymmetric total synthesis of (-)-quinocarcin has been achieved through high step economy using commercially available starting materials. The key chiral pyrrolidine intermediate with three stereocenters was prepared via a catalytic enantioselective reductive 1,3-dipolar cycloaddition reaction. This synthesis also involved a Rh-III-catalyzed C-H activation/cyclization and a tandem diastereoselective hydrogenation/cyclization to construct the tetrahydroisoquinoline-pyrrolidine tetracyclic core unit of quinocarcin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Bartlomiej Sadowski, Dominik Mierzwa, Seongsoo Kang, Marek Grzybowski, Yevgen M. Poronik, Andrzej L. Sobolewski, Dongho Kim, Daniel T. Gryko
Summary: This study describes the photophysical behavior of three cyclophane analogs with the DPND core. By changing the deviation from planarity within the DPND core, intersystem crossing can be induced, resulting in a shift of emission maximum from the green to red region without any synthetic modifications.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Kateryna V. Vygranenko, Yevgen M. Poronik, Manon H. E. Bousquet, Olena Vakuliuk, Denis Jacquemin, Daniel T. Gryko
Summary: The lactone carbonyl group of coumarin derivatives can participate in intramolecular Knoevenagel condensations, allowing the unprecedented direct transformation of coumarins into rhodols. The resulting rhodols, which have two ester groups, exhibit intense orange-red fluorescence.
CHEMICAL COMMUNICATIONS
(2022)
Review
Materials Science, Multidisciplinary
Yevgen M. Poronik, Bartlomiej Sadowski, Kamil Szychta, Frank H. Quina, Valentine Vullev, Daniel T. Gryko
Summary: The electronically excited singlet states of nitroaromatic compounds are typically considered to be non-fluorescent. However, recent reports have shown that certain structural types of nitroaromatics can fluoresce efficiently. This article discusses the design principles for achieving fluorescence in nitroaromatics by combining the strong electron-withdrawing properties of the nitro group with reasonable fluorescence quantum yields. The importance of chromophore architecture, conformation, excited state charge transfer, and solvent polarity in modulating the non-radiative decay channels is also highlighted.
JOURNAL OF MATERIALS CHEMISTRY C
(2022)
Article
Chemistry, Organic
Jaqueline S. A. Badaro, Beata Koszarna, Manon H. E. Bousquet, Erik T. Ouellette, Denis Jacquemin, Daniel T. Gryko
Summary: Benzo[a]indolizines with ordered electron-withdrawing substituents were synthesized. This method allows for refined control of the photophysical properties of the compounds. The ability to substitute various groups on the heterocyclic skeleton offers unprecedented opportunities to study their fate in the excited state.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Lukasz Kielesinski, Irena Deperasinska, Olaf Morawski, Kateryna V. Vygranenko, Erik T. Ouellette, Daniel T. Gryko
Summary: Eleven conjoined coumarins with a chromeno[3,4-c]chromene-6,7-dione skeleton were synthesized by reacting electron-rich phenols with esters of coumarin-3-carboxylic acids, catalyzed by Lewis acids or 4-dimethylaminopyridine. The addition of functional groups at different positions on the heterocyclic skeleton allowed for the production of pi-expanded coumarins with emission properties dependent or independent of solvent polarity. Computational studies provided insights into the solvatochromic effects and the dipole moments of the molecules in different states.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Pawel Kowalczyk, Mariusz Tasior, Shuhei Ozaki, Kenji Kamada, Daniel T. Gryko
Summary: An original approach has been developed for the insertion of formyl substituents at positions 2 and 5 of 1,4-dihydropyrrolo[3,2-b]pyrroles. The synthetic utility of these formyl groups was investigated, and a series of centrosymmetric A-pi-D-pi-A frameworks were constructed. One of the molecules with dicyanovinylidene flanking groups exhibited strong two-photon absorption and can be potentially applied in specific fields.
Article
Chemistry, Multidisciplinary
Heba Megahd, Paola Lova, Samim Sardar, Cosimo D'Andrea, Andrea Lanfranchi, Beata Koszarna, Maddalena Patrini, Daniel T. Gryko, Davide Comoretto
Summary: Controlling the radiative rate of emitters with macromolecular photonic structures allows for enhanced performances. Researchers have demonstrated the use of all-polymer planar microcavities to change the fluorescence lifetime. By utilizing high-index and low-index materials, they achieved a large dielectric contrast and successfully controlled the radiative rate.
Article
Chemistry, Organic
Maciej Krzeszewski, Sylwia Modrzycka, Manon H. E. Bousquet, Denis Jacquemin, Marcin Drag, Daniel T. Gryko
Summary: The properties of electron-donating groups and the connections between them influence the behavior of substituted 1,8-naphthalimide molecules in the excited state. A probe constructed from a selective peptide sequence, a reactive warhead, and the brightest green-emitting fluorophore shows impressive performance in detecting thrombin protease in a newly constructed series of 1,8-naphthalimides.
Article
Chemistry, Multidisciplinary
Charles W. Stark, Matt Rammo, Aleksander Trummal, Merle Uudsemaa, Juri Pahapill, Meelis-Mait Sildoja, Sofja Tshepelevitsh, Ivo Leito, David C. Young, Bartosz Szymanski, Olena Vakuliuk, Daniel T. Gryko, Aleksander Rebane
Summary: The Laporte rule states that one- and two-photon absorption spectra of symmetric molecules should display alternatively forbidden electronic transitions. However, for organic fluorophores, the distinction between symmetric and non-inversion symmetric two-photon spectra is often unclear due to vibronic interactions. In this study, we use protonation to break and then reconstitute inversion symmetry in a symmetric diketopyrrolopyrrole, resulting in significant changes in two-photon absorption. Through experiments and calculations, we explain how low-frequency vibrational modes can lead to deviations from the Laporte rule and propose the system as an inversion symmetry switch for two-photon sensing applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Krzysztof Gorski, Tea Ostojic, Marzena Banasiewicz, Erik T. Ouellette, Luca Grisanti, Daniel T. Gryko
Summary: A heavy metal-free synthetic methodology for the one-step conversion of ketones into 4,5,6,7-tetrafluorobenzofurans (F(4)BFs) has been developed. It has favorable qualities such as the use of readily available substrates, broad scope, scalability, and good reaction yields. The synthesized benzofurans were previously inaccessible, and this methodology also enables the preparation of furo[2,3-b]pyrazines and difuro[2,3-c:3',2'-e]pyridazine, which have not been explored before.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
G. Dinesh Kumar, Marzena Banasiewicz, Antoni Wrzosek, Omar O'Mari, Monika Zochowska, Valentine Vullev, Denis Jacquemin, Adam Szewczyk, Daniel T. Gryko
Summary: Novel fluorescent probes based on the diketopyrrolopyrrole scaffold have been designed and synthesized for highly sensitive detection of zinc cations. These probes exhibit large bathochromic shifts in fluorescence and operate via modulation of intramolecular charge transfer. They show high selectivity towards zinc ions and can be selectively localized in different organelles of cardiac cells.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sebastian Stecko, Daniel T. Gryko
Summary: Heteropentalenes, with two fused five-membered heterocyclic rings, have attracted significant attention due to their relatively easy access and physicochemical properties matching various applications. This Perspective discusses the recent progress of heteropentalenes as active elements in organic light-emitting diodes and organic field-effect transistors.
Article
Chemistry, Multidisciplinary
G. Dinesh Kumar, Marzena Banasiewicz, Antoni Wrzosek, Rafal P. Kampa, Manon H. E. Bousquet, Damian Kusy, Denis Jacquemin, Adam Szewczyk, Daniel T. Gryko
Summary: The study reveals that a compound with a specific structure shows high sensitivity towards K+ and can rapidly regulate the concentration of K+ in mitochondria upon stimulation.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Mariusz Tasior, Pawel Kowalczyk, Marta Przybyl, Malgorzata Czichy, Patryk Janasik, Manon H. E. Bousquet, Mieczyslaw Lapkowski, Matt Rammo, Aleksander Rebane, Denis Jacquemin, Daniel T. Gryko
Summary: A novel doubly B/N-doped ladder-type pyrrolo[3,2-b]pyrroles with strong absorption and efficient fluorescence properties have been developed. Structural modifications lead to significant variations in photophysical properties within the family of these ultrastable dyes. Theoretical calculations support experimental trends, including two-photon absorption, in a nearly quantitative manner.
Article
Chemistry, Multidisciplinary
Bartlomiej Sadowski, Marzena Kaliszewska, Yevgen M. Poronik, Malgorzata Czichy, Patryk Janasik, Marzena Banasiewicz, Dominik Mierzwa, Wojciech Gadomski, Trevor D. Lohrey, John A. Clark, Mieczyslaw Lapkowski, Boleslaw Kozankiewicz, Valentine Vullev, Andrzej L. Sobolewski, Piotr Piatkowski, Daniel T. Gryko
Summary: Nitroaromatics typically do not fluoresce, but by strategically placing nitro groups farther from the core, researchers have achieved some of the highest fluorescence quantum yields ever recorded for nitroaromatics. This strategy, however, may lead to alternative mechanisms for fluorescence quenching involving transitions to dark n pi* singlet states and aborted photochemistry, highlighting the importance of understanding the excited-state dynamics of such compounds for designing highly fluorescent electron-deficient conjugates.
