Design, Synthesis, and Self-Organization of Nature- and Bio-Inspired Homochiral Helical Complex Systems

Virgil Percec; Jasper Adamson; Dipankar Sahoo; Devendra S. Maurya

doi:10.1055/a-2685-2029

Synthesis, Table of Contents

Synthesis
DOI: 10.1055/a-2685-2029

Short Review

Part of the Special Topic Romanian Chemists in Synthesis

Design, Synthesis, and Self-Organization of Nature- and Bio-Inspired Homochiral Helical Complex Systems

Authors

Virgil Percec

¹Chemistry, University of Pennsylvania, Philadelphia, United States (Ringgold ID: RIN6572)
Jasper Adamson

¹Chemistry, University of Pennsylvania, Philadelphia, United States (Ringgold ID: RIN6572)

²School of Engineering, Tallinn University of Technology, Tallinn, Estonia (Ringgold ID: RIN54561)
Dipankar Sahoo

¹Chemistry, University of Pennsylvania, Philadelphia, United States (Ringgold ID: RIN6572)
Devendra S. Maurya

¹Chemistry, University of Pennsylvania, Philadelphia, United States (Ringgold ID: RIN6572)

Abstract

All articles of this category

Abstract

Helical homochirality is available in nature, biology, and, most recently, also in synthetic systems. Selected examples of helical complex systems from nature, biology, and synthetic chemistry will be briefly discussed, most probably for the first time, in a single publication. When available, the mechanisms of the origin of their homochirality will be presented. In order to encourage new discoveries, the historical events of many discoveries will also be highlighted. Potential connections between homochirality in nature and biology, as well as in nature- and bio-inspired macroscopic, molecular, and supramolecular complex systems, will be mentioned.

Keywords

Spiral - Helical - Spherical helix - Homochirality - Self-assembly - Self-organization - Complex systems - Nature- and biological-inspired

Full Text

References

References

1a Frank P, Bonner WA, Zare RN. Keinan E, Schechter I. eds Chemistry for the 21st Century. Weinheim: Wiley-VCH; 2001: 175
1b Blackmond DG. Philos Trans R Soc B 2011; 366: 2878
1c Breslow R. Isr J Chem 2011; 51: 990
1d Frank FC. Biochim Biophys Acta 1953; 11: 459
1e Gal J, Cintas P. Top Curr Chem 2013; 333: 1
1f Rosen BM, Roche C, Percec V. Top Curr Chem 2013; 333: 213
1g Weissbuch L, Lahav M. Chem Rev 2011; 111: 3236
1h Nikolaou KC, Montagnon T. Molecules that Changed the World. Weinheim: Wiley-VCH; 2008
1i Stinson SC. Chem Eng News 2001; 79 (40) 79
1j Ottino JM. Nature 2004; 427: 399
1k Kauffman SA. The Origins of Order: Self-Organization and Selection in Evolution. New York and Oxford: Oxford University Press; 1993
1l Kauffman S. At Home in the Universe: The Search for the Laws of Self-Organization and Complexity. New York and Oxford: Oxford University Press; 1995
1m Camazine S, Deneubourg J-L, Franks NR, Sneyd J, Theraulaz G, Bonabeau E. Self-Organization in Biological Systems. Princeton and Oxford: Princeton University Press; 2003

2 Hubble EP. The Realm of the Nebulae. New Haven, CT: The Silliman Foundation Lectures Series; Yale University Press; 1936

3a Land K, Slosar A, Lintott C. et al. Mem R Astron Soc 2008; 388: 1686
3b Tu S, Chan JCL, Xu J, Zhong Q, Zhou W, Zhang Y. Nat Commun 2022; 13: 7325
3c Hou Z, Zha W, Wang H, Liao W-H, Bowen CR, Cao J. Energy Conv Manag 2022; 259: 115441

4a Hoskins BJ, James IN, White GH. J Atmos Sci 1983; 40: 1595
4b Holton JR, Hakim GJ. An Introduction to Dynamic Meteorology. 5th ed San Diego: Academic Press; 2013: 120-140
4c Leal Filho W, Hunt J, Kovaleva M. J Mar Sci Eng 2021; 9: 1289

5 Coriolis G-G. J Éc Polytech 1835; 15: 142
6 Persson AO. Hist of Meteorol 2005; 2: 1

7a Pedlosky J. Rev Geophys 1987; 25: 377
7b Vallis GK. Atmospheric and Oceanic Fluid Dynamics. Cambridge: Cambridge University Press; 2017: 50

8 Wylie PE. Aeronaut J 1953; 57: 655

9a Leighton RB, Sands M, Treiman SB. Phys Today 1964; 17: 45
9b Halliday D, Resnick R, Walker J. Fundamentals of Physics. Hoboken, NJ: 2014: 48

10 Wylie PE. Aeronaut J 1953; 57: 655
11 Miller D. Sci Am 1974; 230: 32

12a Gill AE. Atmosphere-Ocean Dynamics. San Diego: Academic Press; 1982: 55
12b Lighthill MJ. Geophys J Int 1969; 18: 117

13a Shapiro AH. Nature 1962; 196: 1080
13b Trefethen LM, Bilger RW, Fink PT, Luxton RE, Tanner RI. Nature 1965; 207: 1084

14a Percec V, Xiao Q. Bull Chem Soc Jpn 2021; 94: 900
14b Percec V, Adamson J, Gianti E. In: Supramolecular Nanotechnology. Azzaroni O, Conda-Sheridan M. eds. Vol 1. Wiley; 2023: 1
14c Khan N, Sarwar MK, Rashid M. et al. Sci Rep 2025; 15: 5827
14d Qian C-N, Pezzella F, Lu Z. Vis Cancer Med 2020; 1: E1
14e Perera AS, Coppens M-O. Phil Trans R Soc A 2019; 377: 20180268

15a Pauling L, Corey RB. J Am Chem Soc 1950; 72: 5349
15b Pauling L, Corey RB, Branson HR. Proc Natl Acad Sci USA 1951; 37: 205
15c Crane HR. Sci Mon 1950; 70: 376
15d Kushner DJ. Bacteriol Rev 1969; 33: 302

16 Bragg WL, Kendrew JC, Perutz MF. Proc R Soc Lond A 1950; 203: 321

17a Percec V. Chem 2023; 9: 2041
17b Percec V. Chem 2023; 9: 3386

18a Cochran W, Crick FHC. Nature 1952; 169: 234
18b Cochran W, Crick FH, Vand V. Acta Crystallogr 1952; 5: 581
18c Peterca M, Percec V, Imam MR, Leowanawat P, Morimitsu K, Heiney PA. J Am Chem Soc 2008; 130: 14840

19a Pauling L, Corey RB. Nature 1953; 171: 346
19b Pauling L, Corey RB. Proc Natl Acad Sci USA 1953; 39: 84

20a Watson JD, Crick FHC. Nature 1953; 171: 737
20b Wilkins MHF, Stokes AR, Wilson HR. Nature 1953; 171: 738
20c Franklin RE, Gosling RG. Nature 1953; 171: 740

21a Chargaff E. Heraclitean Fire. Schetches from a Life before Nature. New York: The Rockefeller University Press; 1978
21b Chargaff E, Zamenhof S, Green C. Nature 1950; 165: 756
21c Cohen SS. Proc Am Philos Soc 2004; 148: 221
21d McCarty M. Nature 2003; 421: 406

22a Klug A. Angew Chem Int Ed Engl 1983; 22: 565
22b Klug A. J Mol Biol 2004; 335: 3
22c Franklin RE, Gosling RG. Acta Cryst 1953; 6: 673

23a Percec V, Xiao Q. Chem 2021; 7: 529
23b Percec V, Heck J, Johansson G, Tomazos D, Ungar G. Macromol Symp 1994; 77: 237

24 Bunn CW, Howells ER. Nature 1954; 174: 549

25a Percec V, Leowanawat P. Isr J Chem 2011; 51: 1107
25b Percec V. Isr J Chem 2020; 60: 48

26a Vogl O, Jaycox GD. Polymer 1987; 28: 2179
26b Nakano T, Okamoto Y. Chem Rev 2001; 101: 4013
26c Rowan AE, Nolte RJM. Angew Chem Int Ed 1998; 37: 63

27a Tomalia DA, Khanna SN. Chem Rev 2016; 116: 2705
27b Tomalia DA, Naylor AM, Goddard WA. Angew Chem Int Ed Engl 1990; 29: 138
27c Fischer M, Vögtle F. Angew Chem Int Ed 1999; 38: 884
27d Newkome GR, He E, Moorefield CN. Chem Rev 1999; 99: 1689
27e Tomalia DA, Christensen JB, Boas U. Dendrimers, Dendrons and Dendritic Polymers. Cambridge, UK: Cambridge University Press; 2012

28a Percec V, Heck J. Polym Prepr (Am Chem Soc, Div Polym Chem) 1989; 30: 450
28b Percec V, Heck J. Polym Prepr (Am Chem Soc, Div Polym Chem) 1991; 32: 263
28c Percec V, Heck J. Polym Prepr (Am Chem Soc, Div Polym Chem) 1991; 32: 698
28d Percec V, Heck J. Polym Bull 1990; 24: 255
28e Percec V, Heck J. Polym Bull 1991; 25: 55
28f Percec V, Heck J. Polym Bull 1991; 25: 431
28g Percec V, Heck J. J Polym Sci Part A Polym Chem 1991; 29: 591
28h Percec V, Heck J, Ungar G. Macromolecules 1991; 24: 4957

29a Percec V, Lee M, Heck J, Blackwell HE, Ungar G, Alvarez-Castillo A. J Mater Chem 1992; 2: 931
29b Percec V, Heck J, Tomazos D, Falkenberg F, Blackwell H, Ungar G. J Chem Soc, Perkin Trans 1 1993; 1: 2799
29c Kwon YK, Chvalun S, Schneider A-I, Blackwell J, Percec V, Heck JA. Macromolecules 1994; 27: 6129
29d Kwon YK, Danko C, Chvalun S, Blackwell J, Heck JA, Percec V. Macromol Symp 1994; 87: 103
29e Percec V, Tomazos D, Heck J, Blackwell H, Ungar G. J Chem Soc Perkin Trans 1994; 2: 31
29f Kwon YK, Chvalun SN, Blackwell J, Percec V, Heck JA. Macromolecules 1995; 28: 1552
29g Percec V, Schlueter D, Kwon YK, Blackwell J, Moeller M, Slangen PJ. Macromolecules 1995; 28: 8807
29h Chvalun SN, Kwon YK, Blackwell J, Percec V. Vysokomolekulyarnye Soedineniya Ser A & Ser b 1996; 38: 1978
29i Blackwell J, Chvalun SN, Kwon YK, Percec V. Acta Crystallogr A 1996; 52: C477
29j Chvalun SN, Blackwell J, Kwon YK, Percec V. Macromol Symp 1997; 118: 663
29k Chvalun SN, Blackwell J, Cho JD, Kwon YK, Percec V, Heck JA. Polymer 1998; 39: 4515
29l Chvalun SN, Blackwell J, Cho JD, Bykova IV, Percec V. Acta Polym 1999; 50: 51
29m Chvalun SN, Shcherbina MA, Bykova IV, Blackwell J. Polym Sci Ser A 2001; 43: 33
29n Chvalun SN, Shcherbina MA, Bykova IV, Blackwell J, Percec V. Polym Sci Ser A 2002; 44: 1281
29o Chvalun SN, Shcherbina MA, Yakunin AN, Blackwell J, Percec V. Polym Sci Ser A 2007; 49: 158
29p Shcherbina MA, Bakirov AV, Percec V. Polym Sci Ser A 2008; 50: 166
29q Shcherbina MA, Bakirov AV, Yakunin AN. et al. Crystallogr Rep 2012; 57: 151

30a Percec V, Cho W-D, Ungar G, Yeardley DJP. J Am Chem Soc 2001; 123: 1302
30b Percec V, Mitchell CM, Cho W-D. et al. J Am Chem Soc 2004; 126: 6078
30c Percec V, Holerca MN, Nummelin S. et al. Chem Eur J 2006; 12: 6216
30d Percec V, Peterca M, Sienkowska MJ. et al. J Am Chem Soc 2006; 128: 3324
30e Percec V, Won BC, Peterca M, Heiney PA. J Am Chem Soc 2007; 129: 11265
30f Rosen BM, Wilson DA, Wilson CJ. et al. J Am Chem Soc 2009; 131: 17500
30g Percec V, Wang S, Huang N. et al. J Am Chem Soc 2021; 143: 17724
30h Ungar G, Percec V, Holerca MN, Johansson G, Heck JA. Chem Eur J 2000; 6: 1258
30i Percec V, Cho W-D, Möller M, Prokhorova SA, Ungar G, Yeardley DJP. J Am Chem Soc 2000; 122: 4249
30j Percec V, Aqad E, Peterca M. et al. J Am Chem Soc 2006; 128: 16365
30k Percec V, Ahn C-H, Bera TK, Ungar G, Yeardley DJP. Chem Eur J 1999; 5: 1070
30l Percec V, Cho W-D, Ungar G, Yeardley DJP. Angew Chem Int Ed 2000; 39: 1597
30m Imam MR, Peterca M, Edlund U, Balagurusamy VSK, Percec V. J Polym Sci Part A Polym Chem 2009; 47: 4165
30n Rapp A, Schnell I, Sebastiani D, Brown SP, Percec V, Spiess HW. J Am Chem Soc 2003; 125: 13284
30o Peterca M, Imam MR, Leowanawat P. et al. J Am Chem Soc 2010; 132: 11288
30p Percec V, Peterca M, Tsuda Y. et al. Chem Eur J 2009; 15: 8994
30q Ungar G, Percec V, Zeng X, Leowanawat P. Isr J Chem 2011; 51: 1206
30r Percec V, Hudson SD, Peterca M. et al. J Am Chem Soc 2011; 133: 18479
30s Percec V, Imam MR, Peterca M, Wilson DA, Heiney PA. J Am Chem Soc 2009; 131: 1294
30t Percec V, Glodde M, Bera TK. et al. Nature 2002; 419: 384
30u Percec V, Imam MR, Peterca M. et al. J Am Chem Soc 2009; 131: 7662
30v Percec V, Rudick JG, Peterca M, Heiney PA. J Am Chem Soc 2008; 130: 7503
30w Percec V, Dulcey AE, Peterca M. et al. Angew Chem Int Ed 2005; 44: 6516
30x Percec V, Peterca M, Dulcey AE. et al. J Am Chem Soc 2008; 130: 13079

31a Percec V, Smidrkal J, Peterca M. et al. Chem Eur J 2007; 13: 3989
31b Sahoo D, Peterca M, Aqad E. et al. J Am Chem Soc 2016; 138: 14798
31c Sahoo D, Aqad E, Peterca M, Percec V. Giant 2023; 13: 100138
31d Peterca M, Sahoo D, Imam MR, Xiao Q, Percec V. Giant 2022; 12: 100118
31e Sahoo D, Peterca M, Percec V. J Am Chem Soc 2024; 146: 22943
31f Percec V, Sahoo D. Giant 2022; 12: 100127
31g Ho M-S, Partridge BE, Sun H-J. et al. ACS Comb Sci 2016; 18: 723
31h Sahoo D, Peterca M, Percec V. J Am Chem Soc 2024; 146: 27299
31i Sahoo D, Peterca M, Imam MR, Maurya DS, Percec VJ. Mater Chem B 2024; 12: 12265
31j Sahoo D, Aqad E, Peterca M, Percec V. Giant 2023; 13: 100135

32a Rosen BM, Wilson CJ, Wilson DA, Peterca M, Imam MR, Percec V. Chem Rev 2009; 109: 6275
32b Sun H-J, Zhang S, Percec V. Chem Soc Rev 2015; 44: 3900
32c Roche C, Percec V. Isr J Chem 2013; 53: 30
32d Percec V, Sahoo D, Adamson J. Polymers 2023; 15: 1832
32e Rosen BM, Peterca M, Huang C, Zeng X, Ungar G, Percec V. Angew Chem Int Ed 2010; 49: 7002
32f Percec V, Cho W-D, Ungar G, Yeardley DJP. Chem Eur J 2002; 8: 2011
32g Percec V, Cho W-D, Ungar G. J Am Chem Soc 2000; 122: 10273
32h Percec V, Imam MR, Bera TK, Balagurusamy VSK, Peterca M, Heiney PA. Angew Chem Int Ed 2005; 44: 4739
32i Percec V, Glodde M, Johansson G, Balagurusamy VSK, Heiney PA. Angew Chem Int Ed 2003; 42: 4338
32j Percec V, Holerca MN, Uchida S. et al. Chem Eur J 2002; 8: 1106
32k Percec V, Cho W-D, Mosier PE, Ungar G, Yeardley DJP. J Am Chem Soc 1998; 120: 11061
32l Hudson SD, Jung H-T, Percec V. et al. Science 1997; 278: 449
32m Lee S, Bluemle MJ, Bates FS. Science 2010; 330: 349
32n Percec V, Ungar G, Peterca M. Science 2006; 313: 55
32o Peterca M, Percec V. Science 2010; 330: 333
32p Ungar G, Liu Y, Zeng X, Percec V, Cho W-D. Science 2003; 299: 1208
32q Percec V, Ahn C-H, Ungar G, Yeardley DJP, Möller M, Sheiko SS. Nature 1998; 391: 161
32r Rosen BM, Percec V. Nature 2007; 446: 381
32s Zeng X, Ungar G, Liu Y, Percec V, Dulcey AE, Hobbs JK. Nature 2004; 428: 157
32t Sahoo D, Peterca M, Imam MR, Partridge BE, Xiao Q, Percec V. Giant 2022; 10: 100096
32u Peterca M, Sahoo D, Imam MR, Xiao Q, Percec V. Giant 2022; 12: 100118
32v Sahoo D, Imam MR, Peterca M. et al. J Am Chem Soc 2018; 140: 13478
32w Holerca MN, Sahoo D, Partridge BE. et al. J Am Chem Soc 2018; 140: 16941
32y Percec V, Heck JA, Tomazos D, Ungar G. J Chem Soc Perkin Trans 1993; 2: 2381

33a Dukeson DR, Ungar G, Balagurusamy VSK, Percec V, Johansson GA, Glodde M. J Am Chem Soc 2003; 125: 15974
33b Ungar G, Abramic D, Percec V, Heck JA. Liq Cryst 1996; 21: 73
33c Rudick JG, Percec V. New J Chem 2007; 31: 1083
33d Wilson DA, Andreopoulou KA, Peterca M. et al. J Am Chem Soc 2019; 141: 6162
33e Holerca MN, Sahoo D, Peterca M, Partridge BE, Heiney PA, Percec V. Macromolecules 2017; 50: 375
33f Sahoo D, Peterca M, Aqad E. et al. J Am Chem Soc 2016; 138: 14798

34a Percec V, Bae J-Y, Zhao M, Hill DH. J Org Chem 1995; 60: 1066
34b Percec V, Bae J-Y, Zhao M, Hill DH. J Org Chem 1995; 60: 176
34c Percec V, Bae J-Y, Hill DH. J Org Chem 1995; 60: 1060
34d Percec V, Bae J-Y, Hill DH. J Org Chem 1995; 60: 6895
34e Zhang N, Hoffman DJ, Gutsche N, Gupta J, Percec V. J Org Chem 2012; 77: 5956
34f Leowanawat P, Zhang N, Safi M. et al. J Org Chem 2012; 77: 2885
34g Leowanawat P, Zhang N, Percec V. J Org Chem 2012; 77: 1018
34h Leowanawat P, Zhang N, Resmerita A-M, Rosen BM, Percec V. J Org Chem 2011; 76: 9946
34i Moldoveanu C, Wilson DA, Wilson CJ. et al. J Org Chem 2010; 75: 5438
34j Leowanawat P, Resmerita A-M, Moldoveanu C. et al. J Org Chem 2010; 75: 7822
34k Percec V, Golding GM, Smidrkal J, Weichold O. J Org Chem 2004; 69: 3447
34l Percec V, Bera TK, De BB. et al. J Org Chem 2001; 66: 2104
34m Malineni J, Jezorek R, Zhang N, Percec V. Synthesis 2016; 48: 2808
34n Malineni J, Jezorek R, Zhang N, Percec V. Synthesis 2016; 48: 2795
34o Rosen BM, Quasdorf KW, Wilson DA. et al. Chem Rev 2011; 111: 1346

35a Percec V, Barboiu B. Macromolecules 1995; 28: 7970
35b Percec V, Popov AV, Ramirez-Castillo E. et al. J Am Chem Soc 2002; 124: 4940
35c Percec V, Popov AV, Ramirez-Castillo E, Weichold O. J Polym Sci Part A Polym Chem 2003; 41: 3283
35d Percec V, Guliashvili T, Ladislaw JS. et al. J Am Chem Soc 2006; 128: 14156
35e Rosen BM, Percec V. Chem Rev 2009; 109: 5069
35f Nguyen NH, Kulis J, Sun H-J. et al. Polym Chem 2013; 4: 144
35g Percec V, Barboiu B, Grigoras C, Bera TK. J Am Chem Soc 2003; 125: 6503
35h Percec V, Grigoras C, Kim H-J. J Polym Sci Part A Polym Chem 2004; 42: 505
35i Percec V, Grigoras C, Bera TK, Barboiu B, Bissel P. J Polym Sci Part A Polym Chem 2005; 43: 4894
35j Percec V, Barboiu B, Bera TK, Van Der Sluis M, Grubbs RB, Fréchet JMJ. J Polym Sci Part A Polym Chem 2000; 38: 4776
35k Nguyen NH, Levere ME, Percec V. J Polym Sci Part A Polym Chem 2012; 50: 860
35l Moreno A, Lligadas G, Adamson J, Maurya DS, Percec V. Polymers 2023; 15: 1075
35m Rosen BM, Lligadas G, Hahn C, Percec V. J Polym Sci Part A Polym Chem 2009; 47: 3931
35n Rosen BM, Lligadas G, Hahn C, Percec V. J Polym Sci Part A Polym Chem 2009; 47: 3940
35o Lligadas G, Grama S, Percec V. Biomacromolecules 2017; 18: 2981
35p Lligadas G, Grama S, Percec V. Biomacromolecules 2017; 18: 1039
35q Bensabeh N, Moreno A, Maurya DS. et al. Giant 2023; 15: 100176
35r Levere ME, Nguyen NH, Percec V. Macromolecules 2012; 45: 8267
35s Wilson DA, Wilson CJ, Rosen BM, Percec V. Org Lett 2008; 10: 4879
35t Moldoveanu C, Wilson DA, Wilson CJ, Corcoran P, Rosen BM, Percec V. Org Lett 2009; 11: 4974
35u Wilson DA, Wilson CJ, Moldoveanu C. et al. J Am Chem Soc 2010; 132: 1800
35v Maurya DS, Adamson J, Bensabeh N, Lligadas G, Percec V. J Polym Sci 2023; 61: 959
35w Zhang N, Samanta SR, Rosen BM, Percec V. Chem Rev 2014; 114: 5848
35x Percec V, Rudick JG, Peterca M, Aqad E, Imam MR, Heiney PA. J Polym Sci Part A Polym Chem 2007; 45: 4974
35y Percec V, Obata M, Rudick JG. et al. J Polym Sci Part A Polym Chem 2002; 40: 3509
35z Kunzler J, Percec V. J Polym Sci Part A Polym Chem 1990; 28: 1221

36a Percec V, Grigoras C. J Polym Sci Part A Polym Chem 2005; 43: 5609
36b Monteiro MJ, Sherman SE, Percec V. Chem 2020; 6: 1203
36c Maurya DS, Malik A, Feng X, Bensabeh N, Lligadas G, Percec V. Biomacromolecules 2020; 21: 1902
36d Feng X, Maurya DS, Bensabeh N. et al. Biomacromolecules 2020; 21: 250
36e Holerca MN, Peterca M, Partridge BE. et al. J Am Chem Soc 2020; 142: 15265
36f Percec V, Ahn C-H, Cho W-D. et al. J Am Chem Soc 1998; 120: 8619
36g Percec V, Ahn C-H, Barboiu B. J Am Chem Soc 1997; 119: 12978
36h Jiang X, Fleischmann S, Nguyen NH, Rosen BM, Percec V. J Polym Sci Part A Polym Chem 2009; 47: 5591
36i Jiang X, Rosen BM, Percec V. J Polym Sci Part A Polym Chem 2010; 48: 403
36j Jiang X, Rosen BM, Percec V. J Polym Sci Part A Polym Chem 2010; 48: 2716
36k Levere ME, Nguyen NH, Leng X, Percec V. Polym Chem 2013; 4: 1635
36l Percec V, Lee M. J Macromol Sci, Part A: Pure Appl Chem 1992; 29: 723
36m Percec V, Tomazos D, Pugh C. Macromolecules 1989; 22: 3259
36o Fleischmann S, Percec V. J Polym Sci Part A Polym Chem 2010; 48: 2243
36p Guliashvili T, Percec V. J Polym Sci Part A Polym Chem 2007; 45: 1607
36q Barboiu B, Percec V. Macromolecules 2001; 34: 8626
36r Percec V, Asgarzadeh F. J Polym Sci Part A Polym Chem 2001; 39: 1120
36s Monteiro MJ, Guliashvili T, Percec V. J Polym Sci Part A Polym Chem 1835; 2007: 45
36t Percec V, Lee M. Macromolecules 1991; 24: 2780
36u Rosen BM, Percec V. J Polym Sci Part A Polym Chem 2008; 46: 5663
36v Hatano T, Rosen BM, Percec V. J Polym Sci Part A Polym Chem 2010; 48: 164
36w Percec V, Asandei AD, Asgarzadeh F, Bera TK, Barboiu B. J Polym Sci Part A Polym Chem 2000; 38: 3839
36x Nguyen NH, Percec V. J Polym Sci Part A Polym Chem 2011; 49: 4756
36y Lligadas G, Percec V. J Polym Sci Part A Polym Chem 2008; 46: 3174
36z Fleischmann S, Percec V. J Polym Sci A Polym Chem 2010; 48: 2236

37a Percec V, Sahoo D. Macromol Chem Phys 2024; 12: 2400339
37b Percec V, Sahoo D, Maurya DS. Eur Polym J 2025; 225: 113732
37c Percec V, Sahoo D, Maurya D. Giant 2023; 16: 100193
37d Percec V, Sahoo D. Eur Polym J 2024; 203: 112672
37e Prokhorova SA, Sheiko SS, Ahn C-H, Percec V, Möller M. Macromolecules 1999; 32: 2653
37f Percec V, Tomazos D. Adv Mater 1992; 4: 548
37g Barboiu B, Percec V. Macromolecules 2001; 34: 8626

38a Simionescu CI, Percec V, Dumitrescu SJ. Polym Sci Polym Chem Ed 1977; 15: 2497
38b Simionescu CI, Percec VJ. Polym Sci Polym Lett Ed 1979; 17: 421
38c Simionescu CI, Percec V. Prog Polym Sci 1982; 8: 133
38d Simionescu CI, Dumitrescu S, Grigoras M, Percec V. J Polym Sci Polym Lett Ed 1979; 17: 287
38e Percec V, Rudick JG. Macromolecules 2005; 38: 7241
38f Rudick JG, Percec V. Acc Chem Res 2008; 41: 1641
38g Percec V, Rudick JG, Peterca M. et al. J Am Chem Soc 2005; 127: 15257
38h Simionescu CI, Percec VJ. Polym Sci Polym Chem Ed 1980; 18: 147
38i Simionescu CI, Percec V. J Polym Sci, C Polym Symp 1980; 67: 43
38j Simionescu C, Dumitrescu S, Percec V. J Polym Sci Polym Symp 1978; 64: 209
38k Simionescu CR, Dumitrescu SV, Percec V, Negulescu I, Diaconu I. J Polym Sci Polym Symp 1973; 42: 201
38l Dumitrescu S, Percec V, Simionescu CRI. J Polym Sci Polym Chem Ed 1977; 15: 2893
38m Simionescu C, Dumitrescu S, Percec V. Polym J 1976; 8: 313

39a Shen J, Ikeda N, Bi W, Satoh K, Kamigaito M, Okamoto Y. J Polym Sci Part A Polym Chem 2019; 57: 441
39b Yashima E, Maeda K, Iida H, Furusho Y, Nagai K. Chem Rev 2009; 109: 6102
39c Yashima E, Ousaka N, Taura D, Shimomura K, Ikai T, Maeda K. Chem Rev 2016; 116: 13752
39d Kishimoto Y, Miyatake T, Ikariya T, Noyori R. Macromolecules 1996; 29: 5054
39e Kishimoto Y, Itou M, Miyatake T, Ikariya T, Noyori R. Macromolecules 1995; 28: 6662
39f Kishimoto Y, Eckerle P, Miyatake T, Ikariya T, Noyori R. J Am Chem Soc 1994; 116: 12131
39g Kishimoto Y, Eckerle P, Miyatake T. et al. J Am Chem Soc 1999; 121: 12035
39h Feringa BL, Browne WR. Nat Nanotechnol 2008; 3: 383

40 Pasteur L. Ann Chim Phys 1948; 24: 442
41 Jacques J, Collet A, Wilen SH. Enantiomers, Racemates, and Resolutions. Malabar, Fla: Reissue with corr.; Krieger; 1994

42a Nagayama H, Varshney SK, Goto M. et al. Angew Chem Int Ed 2010; 49: 445
42b Link DR, Natale G, Shao R. et al. Science 1924; 1997: 278

43a Okamoto Y. Percec V. ed Hierarchical Macromolecular Structures: 60 Years after the Staudinger Nobel Prize I. Adv Polym Sci Vol 261. Cham: Springer International Publishing; 2013: 391
43b Hein JE, Huynh Cao B, Viedma C, Kellogg RM, Blackmond DG. J Am Chem Soc 2012; 134: 12629

44a Knowles WS. Angew Chem Int Ed 1998; 2002: 41
44b Noyori R. Angew Chem Int Ed 2008; 2002: 41
44c Sharpless KB. Angew Chem Int Ed 2024; 2002: 41

45a Fouquey C, Lehn J, Levelut A. Adv Mater 1990; 2: 254
45b Gulik-Krzywicki T, Fouquey C, Lehn J. Proc Natl Acad Sci USA 1993; 90: 163
45c Lehn J. Angew Chem Int Ed Engl 1988; 27: 89
45d Addadi L, Weiner S. Nature 2001; 411: 753
45e Snir Y, Kamien RD. Science 2005; 307: 1067
45f Pokroy B, Kang SH, Mahadevan L, Aizenberg J. Science 2009; 323: 237
45g Sisco SW, Moore JS. Chem Sci 2014; 5: 81
45h Fletcher SP, Jagt RBC, Feringa BL. Chem Commun 2007; 2578
45i Korevaar PA, George SJ, Markvoort AJ. et al. Nature 2012; 481: 492
45j Ishida Y, Aida T. J Am Chem Soc 2002; 124: 14017
45k Sato K, Itoh Y, Aida T. Chem Sci 2014; 5: 136
45l Lehn J-M. Proc Natl Acad Sci USA 2002; 99: 4763

46 Roche C, Sun H-J, Prendergast ME. et al. J Am Chem Soc 2014; 136: 7169
47 Roche C, Sun H-J, Leowanawat P. et al. Nat Chem 2016; 8: 80

48a Partridge BE, Wang L, Sahoo D. et al. J Am Chem Soc 2019; 141: 15761
48b Wang L, Partridge BE, Huang N. et al. J Am Chem Soc 2020; 142: 9525
48c Sahoo D, Peterca M, Leowanawat P, Percec V. J Am Chem Soc 2024; 146: 18910

49 Perutz MF. Nature 1951; 167: 1053
50 Percec V, Bera TK, Glodde M, Fu Q, Balagurusamy VSK, Heiney PA. Chem Eur J 2003; 9: 921

51a Peterca M, Imam MR, Hudson SD. et al. ACS Nano 2016; 10: 10480
51b Sahoo D, Peterca M, Aqad E. et al. ACS Nano 2017; 11: 983
51c Sahoo D, Peterca M, Percec V. J Am Chem Soc 2024; 146: 32298
51d Percec V, Huang N, Xiao Q. et al. Giant 2022; 9: 100084
51e Huang N, Xiao Q, Peterca M, Zeng X, Percec V. Mol Phys 2021; 119: e1902586
51f Percec V, Sahoo D. Biomacromolecules 2024; 25: 1353
51g Sahoo D, Peterca M, Aqad E, Partridge BE, Klein ML, Percec V. Polym Chem 2018; 9: 2370

52a Percec V, Dulcey AE, Balagurusamy VSK. et al. Nature 2004; 430: 764
52b Percec V, Dulcey AE, Peterca M. et al. Proc Natl Acad Sci USA 2006; 103: 2518
52c Rosen BM, Peterca M, Morimitsu K. et al. J Am Chem Soc 2011; 133: 5135
52d Percec V, Dulcey AE, Peterca M. et al. J Am Chem Soc 2007; 129: 5992
52e Kaucher MS, Peterca M, Dulcey AE. et al. J Am Chem Soc 2007; 129: 11698
52f Peterca M, Percec V, Dulcey AE. et al. J Am Chem Soc 2006; 128: 6713
52g Percec V. Phil Trans R Soc A 2006; 364: 2709
52h Percec V, Dulcey A, Peterca M. et al. Aust J Chem 2005; 58: 472
52i Agre P. Angew Chem Int Ed 2004; 43: 4278
52j Percec V, Dulcey AE, Peterca M, Ilies M, Sienkowska MJ, Heiney PA. J Am Chem Soc 2005; 127: 17902

53a Su D-D, Barboiu M. Coord Chem Rev 2024; 515: 215973
53b Su D-D, Barboiu M. CCS Chem 2023; 5: 279
53c Huang L-B, Mamiya F, Baaden M, Yashima E, Barboiu M. ACS Appl Mater Interfaces 2023; 15: 40133
53d Dutta C, Krishnamurthy P, Su D. et al. Chem 2023; 9: 2237
53e Andrei IM, Chaix A, Benkhaled BT. et al. J Am Chem Soc 2023; 145: 21213
53f Huang L, Di Vincenzo M, Li Y, Barboiu M. Chem Eur J 2021; 27: 2224
53g Su D, Ulrich S, Barboiu M. Angew Chem Int Ed 2023; 62: e202306265

54a Percec V, Wilson DA, Leowanawat P. et al. Science 2010; 328: 1009
54b Sherman SE, Xiao Q, Percec V. Chem Rev 2017; 117: 6538
54c Peterca M, Percec V, Leowanawat P, Bertin A. J Am Chem Soc 2011; 133: 20507
54d Zhang S, Sun H-J, Hughes AD. et al. Proc Natl Acad Sci USA 2014; 111: 9058
54f Xiao Q, Sherman SE, Wilner SE. et al. Proc Natl Acad Sci USA 2017; 114: E7045
54g Kostina NY, Rahimi K, Xiao Q. et al. Nano Lett 2019; 19: 5732
54h Li S, Xia B, Javed B. et al. ACS Nano 2020; 14: 7398
54i Xiao Q, Rubien JD, Wang Z. et al. J Am Chem Soc 2016; 138: 12655

55a Percec V, Leowanawat P, Sun H-J. et al. J Am Chem Soc 2013; 135: 9055
55b Zhang S, Xiao Q, Sherman SE. et al. J Am Chem Soc 2015; 137: 13334
55c Xiao Q, Zhang S, Wang Z. et al. Proc Natl Acad Sci USA 2016; 113: 1162
55d Rodriguez-Emmenegger C, Xiao Q, Kostina NY. et al. Proc Natl Acad Sci USA 2019; 116: 5376
55e Kopitz J, Xiao Q, Ludwig A. et al. Angew Chem 2017; 129: 14869
55f Ludwig A-K, Michalak M, Xiao Q. et al. Proc Natl Acad Sci USA 2019; 116: 2837
55g Xiao Q, Ludwig A-K, Romanò C. et al. Proc Natl Acad Sci USA 2018; 115: E2509
55h Zhang S, Moussodia R-O, Vértesy S. et al. Proc Natl Acad Sci USA 2015; 112: 5585
55i Zhang S, Moussodia R-O, Murzeau C. et al. Angew Chem Int Ed 2015; 54: 4036
55j Zhang H, Song Y, Zhao J, Zhang J, Zhang Q. Angew Chem Int Ed 2014; 53: 11079
55k Zhang S, Moussodia R, Murzeau C. et al. Ang Chem 2015; 127: 4108
55l Zhang S, Moussodia R-O, Sun H-J. et al. Angew Chem Int Ed 2014; 53: 10899
55m Zhang S, Sun H-J, Hughes AD. et al. ACS Nano 2014; 8: 1554
55n Xiao Q, Yadavalli SS, Zhang S. et al. Proc Natl Acad Sci USA 2016; 113: E1134

56a Zhang D, Atochina-Vasserman EN, Maurya DS. et al. J Am Chem Soc 2021; 143: 12315
56b Zhang D, Atochina-Vasserman EN, Maurya DS. et al. J Am Chem Soc 2021; 143: 17975
56c Lu J, Atochina-Vasserman EN, Maurya DS. et al. SSRN J. 2022
56d Zhang D, Atochina-Vasserman EN, Lu J. et al. J Am Chem Soc 2022; 144: 4746
56e Lu J, Atochina-Vasserman EN, Maurya DS. et al. Pharmaceutics 2023; 15: 1572
56f Lu J, Atochina-Vasserman EN, Maurya DS. et al. J Am Chem Soc 2023; 145: 18760
56g Arshad M, Atochina-Vasserman EN, Chenna SS. et al. Biomacromolecules 2024; 25: 6871
56h Sahoo D, Atochina-Vasserman EN, Maurya DS. et al. J Am Chem Soc 2024; 146: 3627
56i Sahoo D, Atochina-Vasserman EN, Lu J. et al. Biomacromolecules 2025; 26: 726
56j Meshanni JA, Stevenson ER, Zhang D. et al. Nat Commun 1806; 2025: 16
56k Arshad M, Atochina-Vasserman EN, Maurya DS. et al. J Am Chem Soc 2025; 147: 21347