Article
Chemistry, Applied
Fan Lv, Xing Guo, Zhong-Yuan Li, Qinghua Wu, Juanjie Chen, Changjiang Yu, Lijuan Jiao, Erhong Hao
Summary: A copper-catalyzed direct acylation of BODIPYs with aldehydes via C-H bond activation was developed, where acyl radicals were formed from aldehydes using TBHP as the radical initiator and selectively reacted with BODIPYs at the alpha-positions. This reaction showed excellent tolerance towards different functional groups, allowing for effective reaction between heteroaromatic and aliphatic aldehydes with BODIPYs. The alpha-acylated BODIPYs exhibited red-shifted absorption and emission, as well as decreased HOMO and LUMO energies compared to the starting BODIPYs due to the introduction of electron-deficient carbonyl groups. Moreover, removal of the BF2 protecting groups from the alpha-acylated BODIPY provided a efficient access to alpha-acylated dipyrrin, which showed sensitive and selective turn-on fluorescence response towards Zn2+ ion in aqueous buffer solution and living cells.
Article
Chemistry, Inorganic & Nuclear
Bintu Kumar, Anindita Bhatta, Prakriti Saraf, Krishnan Rangan, Madhushree Sarkar, Sivaprasad Mitra, Dalip Kumar
Summary: This study efficiently synthesized various beta-triazolyl tethered BODIPYs using a one-pot protocol. The prepared compounds exhibited red-shifted absorption bands and showed selective recognition of Ni2+ and enhanced fluorescence upon interaction with bovine serum albumin. The results demonstrate the potential applications of these beta-triazolyl BODIPYs in sensing and imaging.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Felicity J. Frank, Paul G. Waddell, Michael J. Hall, Julian G. Knight
Summary: 3,5-Dibromo-8-aryl-BODIPYs are prepared through a double aromatic Finkelstein reaction with NaI in refluxing propionitrile from the corresponding 3,5-dichloro- and 3,5-dibromo- congeners, with yields ranging from 51% to 100%. Rate enhancement is observed for 3,5-dibromo-BODIPYs, suggesting a concerted SNAr mechanism, and the resulting 3,5-diiodo-BODIPYs serve as coupling partners in various reactions for the synthesis of complex BODIPY architectures.
Article
Chemistry, Organic
Long Wang, Qinghua Wu, Zhengxin Kang, Xing Guo, Wei Miao, Zhongxin Li, Huiquan Zuo, Hua Wang, Hongwei Si, Lijuan Jiao, Erhong Hao
Summary: A family of directly β,β-linked BODIPY dimers with amino groups at α-positions were selectively prepared by oxidative coupling reaction of α-amino-substituted BODIPYs. The structure of one representative dimer was elucidated by X-ray diffraction analysis, showing a twisted orientation of two BODIPY units with a dihedral angle of 49°. Compared with the corresponding monomers, these dimers exhibited red-shifted absorptions and emissions along with efficient intersystem crossing, with a quantum yield Φ(Δ) of 43% for dimer 4b in toluene, indicating their potential use as heavy-atom-free photosensitizers.
Article
Biochemistry & Molecular Biology
Caroline Ndung'U, Petia Bobadova-Parvanova, Daniel J. J. LaMaster, Dylan Goliber, Frank R. R. Fronczek, Maria da Graca H. Vicente
Summary: The introduction of electron-withdrawing groups on 8(meso)-pyridyl-BODIPYs increases their fluorescence quantum yields by decreasing electronic charge density. A series of new 8(meso)-pyridyl-BODIPYs with 2-, 3-, or 4-pyridyl groups were synthesized and functionalized with nitro and chlorine groups. The spectroscopic properties of these compounds were investigated experimentally and computationally, revealing enhanced fluorescence in polar solvents with methoxycarbonyl groups, fluorescence quenching with a single nitro group, and fluorescence restoration with a chloro substituent.
Review
Chemistry, Inorganic & Nuclear
Jun Wang, Changjiang Yu, Erhong Hao, Lijuan Jiao
Summary: Aza-BODIPY is an important class of heteroatom-containing BODIPY analogue that can be modified to extend its absorption and emission wavelengths, making it promising for the development of near infrared chromophores and fluorophores.
COORDINATION CHEMISTRY REVIEWS
(2022)
Article
Chemistry, Organic
Jie Zhang, Zuowei Xie
Summary: This paper summarizes the recent developments in base metal-catalyzed regioselective B-H functionalization of carboranes, particularly in the regio- and enantio-selective cage B-H derivatization among ten chemically similar BH vertices in o-carboranes. While precious transition metal-catalyzed cage B-H functionalization has made significant advances in diversely functionalized o-carboranes, research on B-H functionalization via a base metal catalysis strategy has just begun recently.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Zhengxin Kang, Fan Lv, Qinghua Wu, Heng Li, Zhongxin Li, Feng-Xi Wu, Zhaoyun Wang, Lijuan Jiao, Erhong Hao
Summary: A series of directly beta,gamma-linked BODIPY oligomers were synthesized via Pd(II)-catalyzed oxidative C-H cross-coupling, with beta,gamma-linked dimers structurally confirmed by X-ray crystallography. These unprecedented oligomers exhibit red-shifted absorptions and near-infrared emissions, efficient intersystem crossing, and Phi(Delta) values ranging from 12-43%, showing potential as heavy-atom-free photosensitizers.
Article
Biochemical Research Methods
Halil Yilmaz, Gokhan Sevinc, Mustafa Hayvali
Summary: A series of novel symmetrical and unsymmetrical aza-BODIPY compounds were synthesized and characterized with various techniques, showing broad absorption in the near infrared region, high fluorescence quantum yield, and significant singlet oxygen generation capability. These compounds exhibit promising photophysical properties for applications in photodynamic therapy and organic photovoltaic cells in the NIR region.
JOURNAL OF FLUORESCENCE
(2021)
Article
Chemistry, Organic
Bixiang Zhou, Mengjie Guo, Qingjie Pan, Mingbo Zhou, Ling Xu, Yutao Rao, Kaisheng Wang, Bangshao Yin, Jie Zhou, Jianxin Song
Summary: A series of p-extended BODIPY derivatives fused with an indolizine scaffold were successfully synthesized with excellent chemoselectivity and regioselectivity, showing red-shifted absorption and large Stokes shifts.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Soukaina Faarasse, Said El Kazzouli, Otmane Bourzikat, Stephane Bourg, Samia Aci-Seche, Pascal Bonnet, Franck Suzenet, Gerald Guillaumet
Summary: Direct and site-selective C5 and C7 palladium-catalyzed C-H arylations of 4-azaindazole N-oxide have been achieved, leading to the synthesis of potential medicinal compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Paulo Eliandro da Silva Junior, Shaiani Maria Gil de Melo, Murilo Helder de Paula, Ricardo Vessecchi, Till Opatz, James E. H. Day, A. Ganesan, Flavio da Silva Emery
Summary: This article discusses the reactivity of 6-azaindazole and 2,6-naphthyridine, which are important in fragment-based drug discovery. The article introduces selective functionalization methods for pyridone and pyrazole, as well as a new method for selective functionalization of heterocycle 1.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Bharti Yadav, Mangalampalli Ravikanth
Summary: In this article, the syntheses of various functionalized aza-boron-dipyrromethene dyes (aza-BODIPYs) are presented, in which functional groups are directly introduced at the 2- or 6- positions of the aza-BODIPYs or on aryl rings present at the 1-, 3-, 5-, and 7-positions of the aza-BODIPYs. Some of these functionalized aza-BODIPYs have been used for the synthesis of aza-BODIPY-based energy-transfer cassettes and light-harvesting complexes.
Article
Chemistry, Multidisciplinary
Craig D. Smith, Alison Thompson
Summary: The method described in the text involves coupling BPin-substituted F-BODIPYs to aryl halides using a mild and efficient catalyst system, enabling the preparation of highly functionalised F-BODIPYs without the need for the corresponding aryl moiety to be in borylated form.
CANADIAN JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Badr Jismy, Chaima Messaoudi, Hassan Allouchi, Abdellatif Tikad, Hedi M'Rabet, Mohamed Abarbri
Summary: A range of new disubstituted pyrazolo[1,5-a]pyrimidine derivatives were synthesized via sequential site-selective cross-coupling reactions of ethyl 2,6-dibromopyrazolo[1,5-a]pyrimidine-3-carboxylate. After careful optimization, the regiocontrolled Suzuki-Miyaura reaction exhibited excellent selectivity at position C6. The monobrominated compounds were further transformed through arylation, alkynylation, or amination, leading to a novel series of ethyl 2,6-disubstituted pyrazolo[1,5-a]pyrimidine-3-carboxylates. This approach provides an efficient regioselective method for diversification of the chemically and biologically interesting pyrazolo[1,5-a]pyrimidine heterocycle at positions C2 and C6.
SYNTHESIS-STUTTGART
(2023)
Article
Nanoscience & Nanotechnology
Zhijie She, Yangang Cheng, Luoqiang Zhang, Xiaoyu Li, Di Wu, Qiang Guo, Jingbo Lan, Ruilin Wang, Jingsong You
ACS APPLIED MATERIALS & INTERFACES
(2015)
Article
Chemistry, Multidisciplinary
Xurong Qin, Xiaoyu Li, Quan Huang, Hu Liu, Di Wu, Qiang Guo, Jingbo Lan, Ruilin Wang, Jingsong You
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Multidisciplinary
Jing Wang, Dekun Qin, Jingbo Lan, Yangyang Cheng, Shuai Zhang, Qiang Guo, Jie Wu, Di Wu, Jingsong You
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Multidisciplinary
Julien B. Kelber, Naitik A. Panjwani, Di Wu, Rafael Gomez-Bombarelli, Brendon W. Lovett, John J. L. Morton, Harry L. Anderson
Article
Chemistry, Multidisciplinary
Hu Liu, Xingrong Liao, Xiaoyu Li, Di Wu, Qiang Guo, Jie Wu, Shengyou Qian, Jingbo Lan, Ruilin Wang, Jingsong You
Article
Chemistry, Medicinal
Su Yan, Matthew W. Elmes, Simon Tong, Kongzhen Hu, Monaf Awwa, Gary Y. H. Teng, Yunrong Jing, Matthew Freitag, Qianwen Gan, Timothy Clement, Longfei Wei, Joseph M. Sweeney, Olivia M. Joseph, Joyce Che, Gregory S. Carbonetti, Liqun Wang, Diane M. Bogdan, Jerome Falcone, Norbert Smietalo, Yuchen Zhou, Brian Ralph, Hao-Chi Hsu, Huilin Li, Robert C. Rizzo, Dale G. Deutsch, Martin Kaczocha, Iwao Ojima
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2018)
Article
Biochemistry & Molecular Biology
Diane Bogdan, Jerome Falcone, Martha P. Kanjiya, Sang Hoon Park, Gregory Carbonetti, Keith Studholme, Maria Gomez, Yong Lu, Matthew W. Elmes, Norbert Smietalo, Su Yan, Iwao Ojima, Michelino Puopolo, Martin Kaczocha
JOURNAL OF BIOLOGICAL CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Gaocan Li, Feijie Song, Di Wu, Jingbo Lan, Xingyan Liu, Jie Wu, Shuaijun Yang, Dan Xiao, Jingsong You
ADVANCED FUNCTIONAL MATERIALS
(2014)
Article
Chemistry, Multidisciplinary
Yumin Huang, Di Wu, Jingsheng Huang, Qiang Guo, Juan Li, Jingsong You
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Polymer Science
Qiang Guo, Jiaxing Dong, Danyang Wan, Di Wu, Jingsong You
MACROMOLECULAR RAPID COMMUNICATIONS
(2013)
Article
Multidisciplinary Sciences
Jinwoo Kim, Diane M. Bogdan, Matthew W. Elmes, Monaf Awwa, Su Yan, Joyce Che, Garam Lee, Dale G. Deutsch, Robert C. Rizzo, Martin Kaczocha, Iwao Ojima
Article
Biochemistry & Molecular Biology
Changwei Wang, Xin Wang, Yi Sun, Adam K. Taouil, Su Yan, Galina I. Botchkina, Iwao Ojima
BIOORGANIC CHEMISTRY
(2020)
Article
Biochemistry & Molecular Biology
Hao-Chi Hsu, Simon Tong, Yuchen Zhou, Matthew W. Elmes, Su Yang, Martin Kaczocha, Dale G. Deutsch, Robert C. Rizzo, Iwao Ojima, Huilin Li
