Abstract
New synthesis of multi-layer 3D chiral molecules has been developed under novel conditions to give better outcomes. The aggregation-induced emission (AIE), UV irradiation/excitation, charge transfer (CT) and local excited (LE) ππ* transitions have been investigated on a representative individual enantiomer of pseudo C2 asymmetry which was made possibly by differentiating moieties on phosphorous on N-phosphonyl ring of chiral sandwich framework. Meanwhile, a new tandem C-N/C-C coupling reaction was unexpectedly rendered providing a novel access to special benzo[a]carbazoles.
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Corey EJ, Czakó B, Kürti L. Molecules and Medicine. New York: John Wiley & Sons, 2012
Ojima I. Catalytic Asymmetric Synthesis. New York: John Wiley & Sons, 2004
Sherman DH, Tsukamoto S, Williams RM. Science, 2015, 349: 149
Jacobsen EN, Pfaltz A, Yamamoto H. Comprehensive Asymmetric Catalysis: Supplement 1: Volume 1. New York: Springer Science & Business Media, 2003
Carreira EM, Kvaerno L. Classics in Stereoselective Synthesis. New York: John Wiley & Sons, 2009
Nicolaou KC, Snyder SA. Classics in Total Synthesis II. New York: Wiley Online Library, 2003
Li G, Chang HT, Sharpless KB. Angew Chem Int Ed Engl, 1996, 35: 451–454
Doyle MP. J Org Chem, 2006, 71: 9253–9260
Krautwald S, Sarlah D, Schafroth MA, Carreira EM. Science, 2013, 340: 1065–1068
MacMillan DWC. Nature, 2008, 455: 304–308
List B. Synlett, 2001, 2001: 1675–1686
Akiyama T. Chem Rev, 2007, 107: 5744–5758
Zbieg JR, Yamaguchi E, McInturff EL, Krische MJ. Science, 2012, 336: 324–327
Taggi AE, Hafez AM, Lectka T. Acc Chem Res, 2003, 36: 10–19
Cao ZY, Wang X, Tan C, Zhao XL, Zhou J, Ding K. J Am Chem Soc, 2013, 135: 8197–8200
Xie JH, Zhou QL. Acc Chem Res, 2008, 41: 581–593
Cai Y, Liu X, Zhou P, Feng X. J Org Chem, 2018, 84: 1–13
Yu J, Shi F, Gong LZ. Acc Chem Res, 2011, 44: 1156–1171
Liu Y, Li W, Zhang J. Natl Sci Rev, 2017, 4: 326–358
Huang XL, He L, Shao PL, Ye S. Angew Chem Int Ed, 2009, 48: 192–195
Ye CX, Melcamu YY, Li HH, Cheng JT, Zhang TT, Ruan YP, Zheng X, Lu X, Huang PQ. Nat Commun, 2018, 9: 410
Zhu Y, Zhang L, Luo S. J Am Chem Soc, 2014, 136: 14642–14645
Cheng X, Lu H, Lu Z. Nat Commun, 2019, 10: 3549
Zhang J, Zeng X, Yang L, Zhong G. Science, 2018, 360: 23
Zhu T, Liu Y, Smetankova M, Zhuo S, Mou C, Chai H, Jin Z, Chi YR. Angew Chem Int Ed, 2019, 58: 15778–15782
Chen J, Huang Y. Nat Commun, 2014, 5: 3437
Guo W, Wu B, Zhou X, Chen P, Wang X, Zhou YG, Liu Y, Li C. Angew Chem Int Ed, 2015, 54: 4522–4526
Li F, Tian D, Fan Y, Lee R, Lu G, Yin Y, Qiao B, Zhao X, Xiao Z, Jiang Z. Nat Commun, 2019, 10: 1774
Luo J, Zhang T, Wang L, Liao G, Yao Q, Wu Y, Zhan B, Lan Y, Lin X, Shi B. Angew Chem, 2019, 131: 6780–6784
Yang G, Guo D, Meng D, Wang J. Nat Commun, 2019, 10: 3062
Ma DK, Miao CB, Sun JW. J Am Chem Soc, 2019
(a)Zhang J, Yu P, Li SY, Sun H, Xiang SH, Wang JJ, Houk KN, Tan B. Science, 2018, 361: 1087
Lin JS, Li TT, Jiao GY, Gu QS, Cheng JT, Lv L, Liu XY. Angew Chem Int Ed, 2019, 58: 7092–7096
Zhang D, Qiu H, Jiang L, Lv F, Ma C, Hu W. Angew Chem Int Ed, 2013, 52: 13356–13360
Shi SL, Wong ZL, Buchwald SL. Nature, 2016, 532: 353–356
Phipps RJ, Hamilton GL, Toste FD. Nat Chem, 2012, 4: 603–614
Gustafson JL, Lim D, Miller SJ. Science, 2010, 328: 1251–1255
Liu H, Dagousset G, Masson G, Retailleau P, Zhu J. J Am Chem Soc, 2009, 131: 4598–4599
Cui X, Xu X, Lu H, Zhu S, Wojtas L, Zhang XP. J Am Chem Soc, 2011, 133: 3304–3307
Yoon H, Marchese AD, Lautens M. J Am Chem Soc, 2018, 140: 10950–10954
Lorion MM, Maindan K, Kapdi AR, Ackermann L. Chem Soc Rev, 2017, 46: 7399–7420
Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem Rev, 1994, 94: 2483–2547
Sandoval CA, Ohkuma T, Muñiz K, Noyori R. J Am Chem Soc, 2003, 125: 13490–13503
Chen Y, Yekta S, Yudin AK. Chem Rev, 2003, 103: 3155–3212
Zhang Z, Butt NA, Zhang W. Chem Rev, 2016, 116: 14769–14827
Liu Y, Zhang W. Angew Chem Int Ed, 2013, 52: 2203–2206
Shao X, Li K, Malcolmson SJ. J Am Chem Soc, 2018, 140: 7083–7087
Chen D, Timmons C, Chao S, Li G. Eur J Org Chem, 2004, 2004(14): 3097–3101
Chen D, Guo L, Liu J, Kirtane S, Cannon JF, Li G. Org Lett, 2005, 7: 921–924
Jende LN, Vantomme A, Welle A, Brusson JM, Carpentier JF, Kirillov E. J Organomet Chem, 2018, 878: 19–29
Varga V, Pinkas J, Císařová I, Kubišta J, Horáček M, Mach K, Gyepes R. Eur J Inorg Chem, 2018, 2018: 2637–2647
Goodwin CAP, Ortu F, Reta D, Chilton NF, Mills DP. Nature, 2017, 548: 439–442
Guo FS, Day BM, Chen YC, Tong ML, Mansikkamäki A, Layfield RA. Angew Chem Int Ed, 2017, 56: 11445–11449
Dai LX, Tu T, You SL, Deng WP, Hou XL. Acc Chem Res, 2003, 36: 659–667
Fu GC. Acc Chem Res, 2000, 33: 412–420
Ruble JC, Fu GC. J Am Chem Soc, 1998, 120: 11532–11533
Shintani R, Lo MMC, Fu GC. Org Lett, 2000, 2: 3695–3697
Mishra S, Liu J, Aponick A. J Am Chem Soc, 2017, 139: 3352–3355
Vyskočil Š, Meca L, Tišlerová I, Císařová I, Polášek M, Harutyunyan SR, Belokon YN, Stead RMJ, Farrugia L, Lockhart SC, Mitchell WL, Kočovský P. Chem Eur J, 2002, 8: 4633–4648
Jurok R, Cibulka R, Dvořáková H, Hampl F, Hodačová J. Eur J Org Chem, 2010, 2010: 5217–5224
Klívar J, Šámal M, Jančařík A, Vacek J, Bednárová L, Buděšínský M, Fiedler P, Starý I, Stará IG. Eur J Org Chem, 2018, 37: 5164–5178
Isla H, Srebro-Hooper M, Jean M, Vanthuyne N, Roisnel T, Lunkley JL, Muller G, Williams JAG, Autschbach J, Crassous J. Chem Commun, 2016, 52: 5932–5935
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
Wu G, Liu Y, Yang Z, Katakam N, Rouh H, Ahmed S, Unruh D, Surowiec K, Li G. Research, 2019, 2019: 1–11
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. Natl Sci Rev, 2019, https://doi.org/10.1093/nsr/nwz203
An G, Seifert C, Li G. Org Biomol Chem, 2015, 13: 1600–1617
Xie JB, Luo J, Winn TR, Cordes DB, Li G. Beilstein J Org Chem, 2014, 10: 746–751
Kaur P, Wever W, Pindi S, Milles R, Gu P, Shi M, Li G. Green Chem, 2011, 13: 1288–1292
Seifert CW, Paniagua A, White GA, Cai L, Li G. Eur J Org Chem, 2016, 2016: 1714–1719
Kaur P, Pindi S, Wever W, Rajale T, Li G. J Org Chem, 2010, 75: 5144–5150
Seifert CW. Dissertation for the Doctoral Degree. Lubbock: Texas Tech University, 2017
Guram AS, Buchwald SL. J Am Chem Soc, 1994, 116: 7901–7902
Paul F, Patt J, Hartwig JF. J Am Chem Soc, 1994, 116: 5969–5970
Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. Angew Chem Int Ed, 2017, 56: 16136–16179
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
Huang G, Wen R, Wang Z, Li BS, Tang BZ. Mater Chem Front, 2018, 2: 1884–1892
He B, Nie H, Chen L, Lou X, Hu R, Qin A, Zhao Z, Tang BZ. Org Lett, 2015, 17: 6174–6177
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
Zhao Z, He B, Nie H, Chen B, Lu P, Qin A, Tang BZ. Chem Commun, 2014, 50: 1131–1133.
Singh S, Samineni R, Pabbaraja S, Mehta G. Angew Chem Int Ed, 2018, 57: 16847–16851
Sankar E, Karunakaran J, Dhivyapirabha L, Mohanakrishnan AK. ChemistrySelect, 2017, 2: 7899–7903
Adamo C, Barone V. J Chem Phys, 1999, 110: 6158–6170
Grimme S, Antony J, Ehrlich S, Krieg H. J Chem Phys, 2010, 132: 154104
Dunning TH Jr. J Chem Phys, 1989, 90: 1007–1023
Schirmer J. Phys Rev A, 1982, 26: 2395–2416
Trofimov AB, Schirmer J. J Phys B-At Mol Opt Phys, 1995, 28: 2299–2324
Hattig C, Weigend F. J Chem Phys, 2000, 113: 5154–5161
Schäfer A, Huber C, Ahlrichs R. J Chem Phys, 1994, 100: 5829–5835
Martin RL. J Chem Phys, 2003, 118: 4775–4777
Klamt A, Jonas V. J Chem Phys, 1996, 105: 9972–9981
Lunkenheimer B, Köhn A. J Chem Theor Comput, 2012, 9: 977–994
Ahlrichs R, Bär M, Häser M, Horn H, Kölmel C. Chem Phys Lett, 1989, 162: 165–169
Acknowledgements
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.
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Liu, Y., Wu, G., Yang, Z. et al. Multi-layer 3D chirality: new synthesis, AIE and computational studies. Sci. China Chem. 63, 692–698 (2020). https://doi.org/10.1007/s11426-019-9711-x
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DOI: https://doi.org/10.1007/s11426-019-9711-x