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Multi-layer 3D chirality: new synthesis, AIE and computational studies

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  • ReceivedDec 30, 2019
  • AcceptedFeb 24, 2020
  • PublishedApr 2, 2020

Abstract


Acknowledgment

This work was supported by the National Natural Science Foundation of China (91956110, 21672100) and Robert A. Welch Foundation (D-1361, USA). Z. C. acknowledges financial support from Beijing National Laboratory for Molecular Sciences (BNLMS201910). H. L. are grateful for support from the School of Pharmaceutical Science and Technology (SPST), Tianjin University, Tianjin, China, including computer time on the SPST computer cluster Arran. We thank Dr. Kaz Surowiec for the analytic assistance discussion.


Interest statement

The authors declare that they have no conflict of interest.


Contributions statement

These authors contributed equally to this work.


Supplement

The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.


References

[1] Sherman DH, Tsukamoto S, Williams RM. Corey EJ, Czakó B, Kürti L. Molecules and Medicine. New York: John Wiley & Sons, 2012. Google Scholar

[2] Li G, Chang HT, Sharpless KB, Doyle MP. Jacobsen EN, Pfaltz A, Yamamoto H. Comprehensive Asymmetric Catalysis: Supplement 1: Volume 1. New York: Springer Science & Business Media, 2003. Google Scholar

[3] Krautwald S, Sarlah D, Schafroth MA, Carreira EM, MacMillan DWC, List B, Akiyama T, Zbieg JR, Yamaguchi E, McInturff EL, Krische MJ, Taggi AE, Hafez AM, Lectka T. Science, 2013, 340: 1065-1068 CrossRef PubMed Google Scholar

[4] Cao ZY, Wang X, Tan C, Zhao XL, Zhou J, Ding K, Xie JH, Zhou QL, Cai Y, Liu X, Zhou P, Feng X, Yu J, Shi F, Gong LZ, Liu Y, Li W, Zhang J. J Am Chem Soc, 2013, 135: 8197-8200 CrossRef PubMed Google Scholar

[5] Huang XL, He L, Shao PL, Ye S, Ye CX, Melcamu YY, Li HH, Cheng JT, Zhang TT, Ruan YP, Zheng X, Lu X, Huang PQ, Zhu Y, Zhang L, Luo S, Cheng X, Lu H, Lu Z, Zhu T, Liu Y, Smetankova M, Zhuo S, Mou C, Chai H, Jin Z, Chi YR. Angew Chem Int Ed, 2009, 48: 192-195 CrossRef PubMed Google Scholar

[6] Chen J, Huang Y, Guo W, Wu B, Zhou X, Chen P, Wang X, Zhou YG, Liu Y, Li C, Li F, Tian D, Fan Y, Lee R, Lu G, Yin Y, Qiao B, Zhao X, Xiao Z, Jiang Z, Luo J, Zhang T, Wang L, Liao G, Yao Q, Wu Y, Zhan B, Lan Y, Lin X, Shi B, Yang G, Guo D, Meng D, Wang J. Nat Commun, 2014, 5: 3437 CrossRef PubMed Google Scholar

[7] Lin JS, Li TT, Jiao GY, Gu QS, Cheng JT, Lv L, Liu XY, Zhang D, Qiu H, Jiang L, Lv F, Ma C, Hu W. Zhang J, Yu P, Li SY, Sun H, Xiang SH, Wang JJ, Houk KN, Tan B. Science, 2018, 361: 1087. Google Scholar

[8] Shi SL, Wong ZL, Buchwald SL, Phipps RJ, Hamilton GL, Toste FD, Gustafson JL, Lim D, Miller SJ, Liu H, Dagousset G, Masson Ǵ, Retailleau P, Zhu J, Cui X, Xu X, Lu H, Zhu S, Wojtas L, Zhang XP, Yoon H, Marchese AD, Lautens M, Lorion MM, Maindan K, Kapdi AR, Ackermann L. Nature, 2016, 532: 353-356 CrossRef PubMed Google Scholar

[9] Kolb HC, VanNieuwenhze MS, Sharpless KB, Sandoval CA, Ohkuma T, Muñiz K, Noyori R, Chen Y, Yekta S, Yudin AK, Zhang Z, Butt NA, Zhang W, Liu Y, Zhang W. Chem Rev, 1994, 94: 2483-2547 CrossRef Google Scholar

[10] Shao X, Li K, Malcolmson SJ, Chen D, Timmons C, Chao S, Li G, Chen D, Guo L, Liu J, Kirtane S, Cannon JF, Li G. J Am Chem Soc, 2018, 140: 7083-7087 CrossRef PubMed Google Scholar

[11] Jende LN, Vantomme A, Welle A, Brusson JM, Carpentier JF, Kirillov E, Varga V, Pinkas J, Císařová I, Kubišta J, Horáček M, Mach K, Gyepes R. J Organomet Chem, 2018, 878: 19-29 CrossRef Google Scholar

[12] Goodwin CAP, Ortu F, Reta D, Chilton NF, Mills DP, Guo FS, Day BM, Chen YC, Tong ML, Mansikkamäki A, Layfield RA. Nature, 2017, 548: 439-442 CrossRef PubMed Google Scholar

[13] Dai LX, Tu T, You SL, Deng WP, Hou XL, Fu GC. Acc Chem Res, 2003, 36: 659-667 CrossRef PubMed Google Scholar

[14] Ruble JC, Fu GC, Shintani R, Lo MMC, Fu GC. J Am Chem Soc, 1998, 120: 11532-11533 CrossRef Google Scholar

[15] Mishra S, Liu J, Aponick A, Vyskočil Š, Meca L, Tišlerová I, Císařová I, Polášek M, Harutyunyan SR, Belokon YN, Stead RMJ, Farrugia L, Lockhart SC, Mitchell WL, Kočovský P, Jurok R, Cibulka R, Dvořáková H, Hampl F, Hodačová J. J Am Chem Soc, 2017, 139: 3352-3355 CrossRef PubMed Google Scholar

[16] Klívar J, Šámal M, Jančařík A, Vacek J, Bednárová L, Buděšínský M, Fiedler P, Starý I, Stará IG, Isla H, Srebro-Hooper M, Jean M, Vanthuyne N, Roisnel T, Lunkley JL, Muller G, Williams JAG, Autschbach J, Crassous J. Eur J Org Chem, 2018, 37: 5164-5178 CrossRef Google Scholar

[17] Wu G, Liu Y, Yang Z, Katakam N, Rouh H, Ahmed S, Unruh D, Surowiec K, Li G, Wu G, Liu Y, Yang Z, Jiang T, Katakam N, Rouh H, Ma L, Tang Y, Ahmed S, Rahman AU, Huang H, Unruh D, Li G. The first X-ray structure of racemic multi-layered framework was achieved in our lab by one of us (DU) on April 24, 2018 as proven by the original database. Google Scholar

[18] An G, Seifert C, Li G, Xie JB, Luo J, Winn TR, Cordes DB, Li G, Kaur P, Wever W, Pindi S, Milles R, Gu P, Shi M, Li G. Org Biomol Chem, 2015, 13: 1600-1617 CrossRef PubMed Google Scholar

[19] Seifert CW, Paniagua A, White GA, Cai L, Li G, Kaur P, Pindi S, Wever W, Rajale T, Li G. Eur J Org Chem, 2016, 2016: 1714-1719 CrossRef PubMed Google Scholar

[20] Guram AS, Buchwald SL, Paul F, Patt J, Hartwig JF, Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. J Am Chem Soc, 1994, 116: 7901-7902 CrossRef Google Scholar

[21] (a) Hu X, Zhao X, He B, Zhao Z, Zheng Z, Zhang P, Shi X, Kwok RTK, Lam JWY, Qin A, Tang BZ. Research, 2018, 2018: 3152870; (b) Huang G, Wen R, Wang Z, Li BS, Tang BZ. Mater Chem Front, 2018, 2: 1884–1892; (c) He B, Nie H, Chen L, Lou X, Hu R, Qin A, Zhao Z, Tang BZ. Org Lett, 2015, 17: 6174–6177; (d) Chen L, Wang YH, He B, Nie H, Hu R, Huang F, Qin A, Zhou XS, Zhao Z, Tang BZ. Angew Chem Int Ed, 2015, 54: 4231–4235; (e) Zhao Z, He B, Nie H, Chen B, Lu P, Qin A, Tang BZ. Chem Commun, 2014, 50: 1131–1133.. Google Scholar

[22] Singh S, Samineni R, Pabbaraja S, Mehta G, Sankar E, Karunakaran J, Dhivyapirabha L, Mohanakrishnan AK. Angew Chem Int Ed, 2018, 57: 16847-16851 CrossRef PubMed Google Scholar

[23] Adamo C, Barone V. J Chem Phys, 1999, 110: 6158-6170 CrossRef Google Scholar

[24] Grimme S, Antony J, Ehrlich S, Krieg H. J Chem Phys, 2010, 132: 154104 CrossRef PubMed Google Scholar

[25] Dunning TH Jr. J Chem Phys, 1989, 90: 1007-1023 CrossRef Google Scholar

[26] Schirmer J. Phys Rev A, 1982, 26: 2395-2416 CrossRef Google Scholar

[27] Trofimov AB, Schirmer J. J Phys B-At Mol Opt Phys, 1995, 28: 2299-2324 CrossRef Google Scholar

[28] Hättig C, Weigend F. J Chem Phys, 2000, 113: 5154-5161 CrossRef Google Scholar

[29] Schäfer A, Huber C, Ahlrichs R. J Chem Phys, 1994, 100: 5829-5835 CrossRef Google Scholar

[30] Martin RL. J Chem Phys, 2003, 118: 4775-4777 CrossRef Google Scholar

[31] Klamt A, Jonas V. J Chem Phys, 1996, 105: 9972-9981 CrossRef Google Scholar

[32] Lunkenheimer B, Köhn A. J Chem Theor Comput, 2012, 9: 977-994 CrossRef PubMed Google Scholar

[33] Ahlrichs R, Bär M, Häser M, Horn H, Kölmel C. Chem Phys Lett, 1989, 162: 165-169 CrossRef Google Scholar

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