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Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues.

ABSTRACT: The proposed structures of jenamidines A, B, and C (1-3) were revised to jenamidines A1/A2, B1/B2, and C (8-10). Jenamidines A1/A2 (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA (76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.

SUBMITTER: Duvall JR

PROVIDER: S-EPMC2528249 | biostudies-literature | 2006 Oct

REPOSITORIES: biostudies-literature

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Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues.

Duvall Jeremy R JR Wu Fanghui F Snider Barry B BB

The Journal of organic chemistry 20061001 22

The proposed structures of jenamidines A, B, and C (1-3) were revised to jenamidines A1/A2, B1/B2, and C (8-10). Jenamidines A1/A2 (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5-Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropion ...[more]

PMID: 17064037

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Project description:Considering the increased demand and potential of photovoltaic devices in clean, renewable electrical and hi-tech applications, non-fullerene acceptor (NFA) chromophores have gained significant attention. Herein, six novel NFA molecules IBRD1-IBRD6 have been designed by structural modification of the terminal moieties from experimentally synthesized A2-A1-D-A1-A2 architecture IBR for better integration in organic solar cells (OSCs). To exploit the electronic, photophysical and photovoltaic behavior, density functional theory/time dependent-density functional theory (DFT/TD-DFT) computations were performed at M06/6-311G(d,p) functional. The geometry, electrical and optical properties of the designed acceptor molecules were compared with reported IBR architecture. Interestingly, a reduction in bandgap (2.528-2.126 eV), with a broader absorption spectrum, was studied in IBR derivatives (2.734 eV). Additionally, frontier molecular orbital findings revealed an excellent transfer of charge from donor to terminal acceptors and the central indenoindene-core was considered responsible for the charge transfer. Among all the chromophores, IBRD3 manifested the lowest energy gap (2.126 eV) with higher λmax at 734 and 745 nm in gaseous phase and solvent (chloroform), respectively due to the strong electron-withdrawing effect of five end-capped cyano groups present on the terminal acceptor. The transition density matrix map revealed an excellent charge transfer from donor to terminal acceptors. Further, to investigate the charge transfer and open-circuit voltage (Voc), PBDBT donor polymer was blended with acceptor chromophores, and a significant Voc (0.696-1.854 V) was observed. Intriguingly, all compounds exhibited lower reorganization and binding energy with a higher exciton dissociation in an excited state. This investigation indicates that these designed chromophores can serve as excellent electron acceptor molecules in organic solar cells (OSCs) that make them attractive candidates for the development of scalable and inexpensive optoelectronic devices.

Dataset Information

Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues.

Publications

Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues.

Similar Datasets

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