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https://www.readbyqxmd.com/read/28714198/enhancing-performance-of-nonfullerene-acceptors-via-side-chain-conjugation-strategy
#1
Jiayu Wang, Wei Wang, Xiaohui Wang, Yang Wu, Qianqian Zhang, Cenqi Yan, Wei Ma, Wei You, Xiaowei Zhan
A side-chain conjugation strategy in the design of nonfullerene electron acceptors is proposed, with the design and synthesis of a side-chain-conjugated acceptor (ITIC2) based on a 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b']di(cyclopenta-dithiophene) electron-donating core and 1,1-dicyanomethylene-3-indanone electron-withdrawing end groups. ITIC2 with the conjugated side chains exhibits an absorption peak at 714 nm, which redshifts 12 nm relative to ITIC1. The absorption extinction coefficient of ITIC2 is 2...
July 17, 2017: Advanced Materials
https://www.readbyqxmd.com/read/28696657/a-3d-structural-model-of-high-performance-non-fullerene-polymer-solar-cells-as-revealed-by-high-resolution-afm
#2
Shaowei Shi, Xiaofeng Chen, Xubo Liu, Xuefei Wu, Feng Liu, Zhi-Guo Zhang, Yongfang Li, Thomas P Russell, Dong Wang
Rapid improvements in non-fullerene polymer solar cells (PSCs) have brought power conversion efficiencies to over 12%. To further improve device performance, a fundamental understanding of the correlations between structure and performance is essential. In this paper, based on a typical high performance system consisting of J61(one donor-acceptor (D-A) copolymer of benzodithiophene and fluorine substituted benzotriazole) and ITIC (3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone)-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']-dithiophene), a 3D-structural model is directly imaged by employing high resolution atomic force microscopy (AFM)...
July 11, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28667874/recent-developments-in-biological-activities-of-indanones
#3
REVIEW
Siddappa A Patil, Renukadevi Patil, Shivaputra A Patil
Indanone is one of the privileged structures in medicinal chemistry and it's commonly associated with various pharmacologically active compounds. The indanone moiety is found in several natural compounds and also, it can be used as intermediate in the synthesis of many different types of medicinally important molecules. Among the medicinally important indanones, the most significant drug probably is donepezil (IV), an acetylcholinesterase (AChE) inhibitor, which has been approved by the US Food and Drug Administration for the treatment of Alzheimer's disease (AD)...
June 21, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28660755/highly-efficient-inverted-d-a1-a2-ternary-blend-organic-photovoltaics-combining-a-ladder-type-non-fullerene-acceptor-and-a-fullerene-acceptor
#4
Shao-Ling Chang, Fong-Yi Cao, Wen-Chia Huang, Po-Kai Huang, Chain-Shu Hsu, Yen-Ju Cheng
A formylated benzodi(cyclopentadithiophene) (BDCPDT) ladder-type structure with forced coplanarity is coupled with two 1,1-dicyanomethylene-3-indanone (IC) moieties via olefination to form a non-fullerene acceptor, BDCPDT-IC. The BDCPDT-IC, as an acceptor (A1) with broad light-absorbing ability and excellent solution processability, is combined with a second PC71BM acceptor (A2) and a medium band gap polymer, PBDB-T, as the donor (D) to form a ternary blend with gradient HOMO/LUMO energy alignments and panchromatic absorption...
July 13, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28613859/donepezil-based-central-acetylcholinesterase-inhibitors-by-means-of-a-bio-oxidizable-prodrug-strategy-design-synthesis-and-in-vitro-biological-evaluation
#5
Ludovic Peauger, Rabah Azzouz, Vincent Gembus, Mihaela-Liliana Ţînţaş, Jana Sopková-de Oliveira Santos, Pierre Bohn, Cyril Papamicaël, Vincent Levacher
With the aim of reducing side effects of acetylcholinesterase inhibitors (AChEIs) during symptomatic treatment of Alzheimer's disease, we report herein a new class of donepezil-based "bio-oxidizable" prodrugs 1 designed to be converted into dual binding site AChEIs 2. While most of indanone-derived N-benzylpyridinium salts 2 revealed to be highly potent dual binding site hAChEIs (IC50 up to 3 nM), outperforming the standard drug donepezil (IC50 = 11 nM), most of the corresponding 1,4-dihydropyridines 1 were found to be inactive...
June 29, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28608531/fused-hexacyclic-nonfullerene-acceptor-with-strong-near-infrared-absorption-for-semitransparent-organic-solar-cells-with-9-77-efficiency
#6
Wei Wang, Cenqi Yan, Tsz-Ki Lau, Jiayu Wang, Kuan Liu, Yan Fan, Xinhui Lu, Xiaowei Zhan
A fused hexacyclic electron acceptor, IHIC, based on strong electron-donating group dithienocyclopentathieno[3,2-b]thiophene flanked by strong electron-withdrawing group 1,1-dicyanomethylene-3-indanone, is designed, synthesized, and applied in semitransparent organic solar cells (ST-OSCs). IHIC exhibits strong near-infrared absorption with extinction coefficients of up to 1.6 × 10(5) m(-1) cm(-1) , a narrow optical bandgap of 1.38 eV, and a high electron mobility of 2.4 × 10(-3) cm(2) V(-1) s(-1) . The ST-OSCs based on blends of a narrow-bandgap polymer donor PTB7-Th and narrow-bandgap IHIC acceptor exhibit a champion power conversion efficiency of 9...
June 13, 2017: Advanced Materials
https://www.readbyqxmd.com/read/28600079/synthesis-antiviral-evaluation-and-molecular-docking-studies-of-n-4-aryl-substituted-unsubstituted-thiosemicarbazones-derived-from-1-indanones-as-potent-anti-bovine-viral-diarrhea-virus-agents
#7
María C Soraires Santacruz, Matías Fabiani, Eliana F Castro, Lucía V Cavallaro, Liliana M Finkielsztein
A series of N(4)-arylsubstituted thiosemicarbazones derived from 1-indanones and a set of compounds lacking such substitution in the N(4) position of the thiosemicarbazone moiety were synthesized and evaluated for their anti-bovine viral diarrhea virus (BVDV) activity. Among these, derivatives 2 and 15 displayed high activity (EC50=2.7±0.4 and 0.7±0.1µM, respectively) as inhibitors of BVDV replication. Novel key structural features related to the anti-BVDV activity were identified by structure-activity relationship (SAR) analysis...
May 27, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28585823/copper-catalyzed-radical-cascade-difluoromethylation-cyclization-of-2-3-arylpropioloyl-benzaldehydes-a-route-to-difluoromethylated-naphthoquinones
#8
Yan Zhang, Shangyi Ye, Mingming Ji, Lisha Li, Dongmei Guo, Gangguo Zhu
A novel copper-catalyzed cascade difluoromethylation/cyclization of 2-(3-arylpropioloyl)benzaldehydes has been developed. This method affords an efficient and straightforward access to structurally diverse difluoromethylated naphthoquinones in one pot, starting from readily available starting materials. The reaction represents the first trans-acyldifluoromethylation of internal alkynes, which features aldehydes as acceptors for the addition of alkenyl radicals. Furthermore, this protocol can also access to monofluoromethylated naphthoquinone and difluoromethylated indanones in the same reaction condition...
June 12, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28570073/efficient-and-stable-ternary-organic-solar-cells-based-on-two-planar-nonfullerene-acceptors-with-tunable-crystallinity-and-phase-miscibility
#9
Jialin Wang, Jiajun Peng, Xiaoyu Liu, Ziqi Liang
Planar perylene diimides (PDIs), when used as nonfullerene acceptors for organic photovoltaics, are constrained by their large π-aggregation in solid state. To tackle this issue, another planar nonfullerene acceptor 3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone)-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene (ITIC) with weak crystallinity and near-infrared light absorption is introduced into the PTB7-Th:PDI binary blend to fabricate efficient and stable ternary solar cells...
June 21, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28560364/copper-catalyzed-acyltrifluoromethylation-of-alkenes-rapid-access-to-trifluoroethyl-indanones-and-related-compounds
#10
Zhicheng Liu, Yihui Bai, Jian Zhang, Yongqi Yu, Ze Tan, Gangguo Zhu
Copper-catalyzed acyltrifluoromethylation of alkenes has been developed for the first time, affording trifluoroethyl indanones and related cyclic ketones in promising yields with excellent diastereoselectivity. The fast incorporation of CF3 and indanone into a single molecule renders it an efficient and valuable tool for the synthesis of biologically active compounds.
May 31, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28557142/reaction-acceleration-in-thin-films-with-continuous-product-deposition-for-organic-synthesis
#11
Zhenwei Wei, Michael Wleklinski, Christina Ferreira, R Graham Cooks
Thin film formats are used to study the Claisen-Schmidt base-catalyzed condensation of 6-hydroxy-1-indanone with substituted benzaldehydes and to compare the reaction acceleration relative to the bulk. Relative acceleration factors initially exceeded 10(3) and were on the order of 10(2) at steady state, although the confined volume reaction was not electrostatically driven. Substituent effects were muted compared to those in the corresponding bulk and microdroplet reactions and it is concluded that the rate-limiting step at steady state is reagent transport to the interface...
May 29, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28526475/identification-and-preliminary-structure-activity-relationships-of-1-indanone-derivatives-as-novel-indoleamine-2-3-dioxygenase-1-ido1-inhibitors
#12
Dingding Gao, Yingxia Li
Indoleamine 2,3-dioxygenase 1 (IDO1) plays a vital role in the catabolism of tryptophan along with the kynurenine pathway which is involved in many human diseases including cancer, Alzheimer's disease, etc. In this study, compound 1 bearing a 1-Indanone scaffold was identified as a novel IDO1 inhibitor by structure-based virtual screening, with moderate to good enzymatic and cellular inhibitory activities. Also, surface plasmon resonance analysis validated the direct interaction between compound 1 and IDO1 protein...
May 10, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28504882/visible-light-induced-tandem-radical-addition-cyclization-of-alkenyl-aldehydes-leading-to-indanones-and-related-compounds
#13
Danyang Lu, Yimei Wan, Lichun Kong, Gangguo Zhu
Herein we describe a novel, visible light-induced tandem radical addition-cyclization of alkenyl aldehydes with α-bromocarbonyl compounds. A set of cyclic ketones, including indanones, cyclopentenones, 3,4-dihydronaphthalen-1(2H)-ones, and chroman-4-ones, are synthesized at room temperature with high efficiency and good functional group compatibility. It represents the first report on the catalytic 1,2-acylalkylation of unactivated alkenes.
May 15, 2017: Organic Letters
https://www.readbyqxmd.com/read/28481313/two-new-metabolites-from-the-endophytic-fungus-alternaria-sp-a744-derived-from-morinda-officinalis
#14
Ying Wang, Hong-Xin Liu, Yu-Chan Chen, Zhang-Hua Sun, Hao-Hua Li, Sai-Ni Li, Ming-Li Yan, Wei-Min Zhang
Two new compounds isobenzofuranone A (1) and indandione B (2), together with eleven known compounds (3-13) were isolated from liquid cultures of an endophytic fungus Alternaria sp., which was obtained from the medicinal plant Morinda officinalis. Among them, the indandione (2) showed a rarely occurring indanone skeleton in natural products. Their structures were elucidated mainly on the basis of extensive spectroscopic data analysis. All of the compounds were evaluated with cytotoxic and α-glucosidase inhibitory activity assays...
May 8, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28384544/design-synthesis-and-structure-activity-relationship-study-of-halogen-containing-2-benzylidene-1-indanone-derivatives-for-inhibition-of-lps-stimulated-ros-production-in-raw-264-7-macrophages
#15
Aarajana Shrestha, Hye Jin Oh, Mi Jin Kim, Nirmala Tilija Pun, Til Bahadur Thapa Magar, Ganesh Bist, Hongseok Choi, Pil-Hoon Park, Eung-Seok Lee
As a continuous effort to discover new potential anti-inflammatory agents, we systematically designed and synthesized sixty-one 2-benzylidene-1-indanone derivatives with structural modification of chalcone, and evaluated their inhibitory activity on LPS-stimulated ROS production in RAW 264.7 macrophages. Systematic structure-activity relationship study revealed that hydroxyl group in C-5, C-6, or C-7 position of indanone moiety, and ortho-, meta-, or para-fluorine, trifluoromethyl, trifluoromethoxy, and bromine functionalities in phenyl ring are important for inhibition of ROS production in LPS-stimulated RAW 264...
March 27, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28382183/synthesis-of-1-indanones-with-a-broad-range-of-biological-activity
#16
REVIEW
Marika Turek, Dorota Szczęsna, Marek Koprowski, Piotr Bałczewski
This comprehensive review describes methods for the preparation of 1-indanones published in original and patent literature from 1926 to 2017. More than 100 synthetic methods utilizing carboxylic acids, esters, diesters, acid chlorides, ketones, alkynes, alcohols etc. as starting materials, have been performed. This review also covers the most important studies on the biological activity of 1-indanones and their derivatives which are potent antiviral, anti-inflammatory, analgesic, antimalarial, antibacterial and anticancer compounds...
2017: Beilstein Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28377529/catabolism-of-the-last-two-steroid-rings-in-mycobacterium-tuberculosis-and-other-bacteria
#17
Adam M Crowe, Israël Casabon, Kirstin L Brown, Jie Liu, Jennifer Lian, Jason C Rogalski, Timothy E Hurst, Victor Snieckus, Leonard J Foster, Lindsay D Eltis
Most mycolic acid-containing actinobacteria and some proteobacteria use steroids as growth substrates, but the catabolism of the last two steroid rings has yet to be elucidated. In Mycobacterium tuberculosis, this pathway includes virulence determinants and has been proposed to be encoded by the KstR2-regulated genes, which include a predicted coenzyme A (CoA) transferase gene (ipdAB) and an acyl-CoA reductase gene (ipdC). In the presence of cholesterol, ΔipdC and ΔipdAB mutants of either M. tuberculosis or Rhodococcus jostii strain RHA1 accumulated previously undescribed metabolites: 3aα-H-4α(carboxyl-CoA)-5-hydroxy-7aβ-methylhexahydro-1-indanone (5-OH HIC-CoA) and (R)-2-(2-carboxyethyl)-3-methyl-6-oxocyclohex-1-ene-1-carboxyl-CoA (COCHEA-CoA), respectively...
April 4, 2017: MBio
https://www.readbyqxmd.com/read/28345917/enantiodivergent-synthesis-of-tertiary-%C3%AE-aryl-1-indanones-evidence-toward-disparate-mechanisms-in-the-palladium-catalyzed-decarboxylative-asymmetric-protonation
#18
Cian Kingston, Patrick J Guiry
Herein, we describe a study into the scope and origin of an enantiodivergent effect in the palladium-catalyzed decarboxylative asymmetric protonation. By switching the achiral proton source, both enantiomers of a series of tertiary α-aryl-1-indanones are readily accessed from the corresponding α-aryl-β-keto allyl esters. In this example of dual stereocontrol, enantioselectivities up to 94% (S) and 92% (R) were achieved using Meldrum's acid and formic acid, respectively. In an attempt to rationalize this switch in absolute configuration an investigation of the ambiguous mechanism of the decarboxylative asymmetric protonation was conducted...
March 27, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28333391/high-performance-nonfullerene-polymer-solar-cells-based-on-imide-functionalized-wide-bandgap-polymers
#19
Baobing Fan, Kai Zhang, Xiao-Fang Jiang, Lei Ying, Fei Huang, Yong Cao
High-performance nonfullerene polymer solar cells (PSCs) are developed by integrating the nonfullerene electron-accepting material 3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone))-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophne) (ITIC) with a wide-bandgap electron-donating polymer PTzBI or PTzBI-DT, which consists of an imide functionalized benzotriazole (TzBI) building block. Detailed investigations reveal that the extension of conjugation can affect the optical and electronic properties, molecular aggregation properties, charge separation in the bulk-heterojunction films, and thus the overall photovoltaic performances...
June 2017: Advanced Materials
https://www.readbyqxmd.com/read/28296421/silver-catalyzed-regioselective-fluorination-of-carbonyl-directed-alkynes-synthesis-of-%C3%AE-fluoroketones
#20
Fang-Hui Li, Zhong-Jian Cai, Ling Yin, Jian Li, Shun-Yi Wang, Shun-Jun Ji
A novel silver-catalyzed fluorination reaction of carbonyl directed alkynes in the presence of N-fluorobenzenesulfonimide and water with high regioselectivities has been developed. The established protocol provides an alternative method for rapid assembly of α-fluoroketone derivatives under simple and mild reaction conditions. The reaction pathway involves a ring closure and opening process for the construction of new C-O and C-F bonds. In addition, a fluorine-containing indanone was observed through further N-heterocyclic carbene catalyzed intramolecular crossed-benzoin reaction of α-fluoroketone...
April 7, 2017: Organic Letters
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