Abstract
Nucleation from solution is fundamental to many natural and industrial processes. The understanding of molecular mechanism of nucleation from solution is conducive to predict crystal structure, control polymorph and design desired crystal materials. In this review, the nucleation theories, including classical nucleation theory (CNT), nonclassical nucleation theory, as well as other new proposed theories, were reprised, and the molecular mechanism of these theories was compared. Then, the molecular process of nucleation, including the current study techniques, the effect of molecular self-assembly in solutions, desolvation process, as well as the properties of solvent and crystal structure on nucleation from solution were summarized. Furthermore, the relationship of molecular conformation in solution and in crystal, and the effect of solute molecular flexibility on nucleation were discussed. Finally, the current challenges and future scopes of crystal nucleation from solution were discussed.
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Myerson AS, Trout BL. Science, 2013, 341: 855–856
Tsarfati Y, Rosenne S, Weissman H, Shimon LJW, Gur D, Palmer BA, Rybtchinski B. ACS Cent Sci, 2018, 4: 1031–1036
Shahar C, Dutta S, Weissman H, Shimon LJW, Ott H, Rybtchinski B. Angew Chem Int Ed, 2016, 55: 179–182
Davey RJ. Nature, 2004, 428: 374–375
Davey RJ, Allen K, Blagden N, Cross WI, Lieberman HF, Quayle MJ, Righini S, Seton L, Tiddy GJT. CrystEngComm, 2002, 4: 257–264
Mirabello G, Ianiro A, Bomans PHH, Yoda T, Arakaki A, Friedrich H, de With G, Sommerdijk NAJM. Nat Mater, 2020, 19: 391–396
Chen H, Li M, Lu Z, Wang X, Yang J, Wang Z, Zhang F, Gu C, Zhang W, Sun Y, Sun J, Zhu W, Guo X. Nat Commun, 2019, 10: 3872
Chen J, Zhu E, Liu J, Zhang S, Lin Z, Duan X, Heinz H, Huang Y, De Yoreo JJ. Science, 2018, 362: 1135–1139
Edkins K, Cruz-Cabeza AJ. CrystEngComm, 2019, 21: 2031–2033
Shiau LD. Crystals, 2019, 9: 69
Cruz-Cabeza AJ, Reutzel-Edens SM, Bernstein J. Chem Soc Rev, 2015, 44: 8619–8635
Nangia A. Acc Chem Res, 2008, 41: 595–604
Cruz-Cabeza AJ, Bernstein J. Chem Rev, 2014, 114: 2170–2191
Davey RJ, Schroeder SLM, ter Horst JH. Angew Chem Int Ed, 2013, 52: 2166–2179
Van Driessche AES, Van Gerven N, Bomans PHH, Joosten RRM, Friedrich H, Gil-Carton D, Sommerdijk NAJM, Sleutel M. Nature, 2018, 556: 89–94
Vekilov PG. Cryst Growth Des, 2004, 4: 671–685
Vekilov PG. Cryst Growth Des, 2010, 10: 5007–5019
Vekilov PG. Nat Mater, 2012, 11: 838–840
Gebauer D, Cölfen H. Nano Today, 2011, 6: 564–584
Gebauer D, Kellermeier M, Gale JD, Bergström L, Cölfen H. Chem Soc Rev, 2014, 43: 2348–2371
Rao A, Cölfen H. Chem Rec, 2018, 18: 1203–1221
Erdemir D, Lee AY, Myerson AS. Acc Chem Res, 2009, 42: 621–629
Zahn D. ChemPhysChem, 2015, 16: 2069–2075
Gebauer D, Raiteri P, Gale JD, Cölfen H. Am J Sci, 2018, 318: 969–988
Kashchiev D. J Cryst Growth, 2020, 530: 125300
Karthika S, Radhakrishnan TK, Kalaichelvi P. Cryst Growth Des, 2016, 16: 6663–6681
Lee J, Yang J, Kwon SG, Hyeon T. Nat Rev Mater, 2016, 1: 16034
Jehannin M, Rao A, Cölfen H. J Am Chem Soc, 2019, 141: 10120–10136
Davey RJ, Back KR, Sullivan RA. Faraday Discuss, 2015, 179: 9–26
Sosso GC, Chen J, Cox SJ, Fitzner M, Pedevilla P, Zen A, Michaelides A. Chem Rev, 2016, 116: 7078–7116
Addicoat M, Adjiman CS, Arhangelskis M, Beran GJO, Bowskill D, Brandenburg JG, Braun DE, Burger V, Cole J, Cruz-Cabeza AJ, Day GM, Deringer VL, Guo R, Hare A, Helfferich J, Hoja J, Iuzzolino L, Jobbins S, Marom N, McKay D, Mitchell JBO, Mohamed S, Neumann M, Nilsson Lill S, Nyman J, Oganov AR, Piaggi P, Price SL, Reutzel-Edens S, Rietveld I, Ruggiero M, Ryder MR, Sastre G, Schön JC, Taylor C, Tkatchenko A, Tsuzuki S, van den Ende J, Woodley SM, Woollam G, Zhu Q. Faraday Discuss, 2018, 211: 325–381
Mullin WJ. Crystallization. Oxford: Butterworth-Heinemann, 2001
Kashchiev D, van Rosmalen GM. Cryst Res Technol, 2003, 38: 555–574
Tang W, Li S, Gong J. Chem Ind Eng, 2018, 35: 2–11
Schüth F. Curr Opin Solid State Mater Sci, 2001, 5: 389–395
Baumgartner J, Dey A, Bomans PHH, Le Coadou C, Fratzl P, Sommerdijk NAJM, Faivre D. Nat Mater, 2013, 12: 310–314
Sleutel M, Lutsko J, Van Driessche AES, Durán-Olivencia MA, Maes D. Nat Commun, 2014, 5: 1–8
Savage JR, Dinsmore AD. Phys Rev Lett, 2009, 102: 198302
ten Wolde PR, Frenkel D. Science, 1997, 277: 1975–1978
Talanquer V, Oxtoby DW. J Chem Phys, 1998, 109: 223–227
Gavezzotti A. Chem Eur J, 1999, 5: 567–576
Warzecha M, Guo R, M. Bhardwaj R, Reutzel-Edens SM, Price SL, Lamprou DA, Florence AJ. Cryst Growth Des, 2017, 17: 6382–6393
Ito F, Suzuki Y, Fujimori J-i, Sagawa T, Hara M, Seki T, Yasukuni R, De La Chapelle ML. Sci Rep, 2016, 6: 22918
Wiedenbeck E, Kovermann M, Gebauer D, Cölfen H. Angew Chem Int Ed, 2019, 58: 19103–19109
Svärd M, Renuka Devi K, Khamar D, Mealey D, Cheuk D, Zeglinski J, Rasmuson ÅC. Phys Chem Chem Phys, 2018, 20: 15550–15559
Xing J, Schweighauser L, Okada S, Harano K, Nakamura E. Nat Commun, 2019, 10: 3608
Kellermeier M, Rosenberg R, Moise A, Anders U, Przybylski M, Cölfen H. Faraday Discuss, 2012, 159: 23–45
Demichelis R, Raiteri P, Gale JD, Quigley D, Gebauer D. Nat Commun, 2011, 2: 1–8
Gebauer D, Völkel A, Cölfen H. Science, 2008, 322: 1819–1822
Pouget EM, Bomans PHH, Goos JACM, Frederik PM, de With G, Sommerdijk NAJM. Science, 2009, 323: 1455–1458
Wallace AF, Hedges LO, Fernandez-Martinez A, Raiteri P, Gale JD, Waychunas GA, Whitelam S, Banfield JF, De Yoreo JJ. Science, 2013, 341: 885–889
Nielsen MH, Aloni S, De Yoreo JJ. Science, 2014, 345: 1158–1162
De Yoreo J. Nat Mater, 2013, 12: 284–285
Smeets PJM, Finney AR, Habraken WJEM, Nudelman F, Friedrich H, Laven J, De Yoreo JJ, Rodger PM, Sommerdijk NAJM. Proc Natl Acad Sci USA, 2017, 114: E7882–E7890
Avaro JT, Wolf SLP, Hauser K, Gebauer D. Angew Chem Int Ed, 2020, 59: 6155–6159
Li D, Nielsen MH, Lee JRI, Frandsen C, Banfield JF, De Yoreo JJ. Science, 2012, 336: 1014–1018
De Yoreo JJ, Gilbert PUPA, Sommerdijk NAJM, Penn RL, Whitelam S, Joester D, Zhang H, Rimer JD, Navrotsky A, Banfield JF, Wallace AF, Michel FM, Meldrum FC, Cölfen H, Dove PM. Science, 2015, 349: aaa6760
Li H, Chavez AD, Li H, Li H, Dichtel WR, Bredas JL. J Am Chem Soc, 2017, 139: 16310–16318
Li H, Evans AM, Castano I, Strauss MJ, Dichtel WR, Bredas JL. J Am Chem Soc, 2020, 142: 1367–1374
Han Y. Nat Mater, 2020, 19: 377–378
Ou Z, Wang Z, Luo B, Luijten E, Chen Q. Nat Mater, 2020, 19: 450–455
Kelly RC, Rodriguez-Hornedo N. Org Process Res Dev, 2009, 13: 1291–1300
Rodríguez Ortega PG, Montejo Gámez M, Márquez López F, López González JJ. Chem Asian J, 2016, 11: 1798–1803
Kulkarni SA, McGarrity ES, Meekes H, ter Horst JH. Chem Commun, 2012, 48: 4983–4985
Khamar D, Zeglinski J, Mealey D, Rasmuson ÅC. J Am Chem Soc, 2014, 136: 11664–11673
Wang N, Hao H, Lu H, Xu R. CrystEngComm, 2017, 19: 3746–3752
Wang N, Huang X, Chen L, Yang J, Li X, Ma J, Bao Y, Li F, Yin Q, Hao H. IUCrJ, 2019, 6: 1064–1073
Kovalchuk MV, Blagov AE, Dyakova YA, Gruzinov AY, Marchenkova MA, Peters GS, Pisarevsky YV, Timofeev VI, Volkov VV. Cryst Growth Des, 2016, 16: 1792–1797
Burton RC, Ferrari ES, Davey RJ, Finney JL, Bowron DT. J Phys Chem B, 2010, 114: 8807–8816
Burton RC, Ferrari ES, Davey RJ, Hopwood J, Quayle MJ, Finney JL, Bowron DT. Cryst Growth Des, 2008, 8: 1559–1565
Peral F, Gallego E. J Mol Structure, 1997, 415: 187–196
Di Tommaso D, Watson KL. J Phys Chem A, 2014, 118: 11098–11113
Redivo L, Anastasiadi RM, Pividori M, Berti F, Peressi M, Di Tommaso D, Resmini M. Phys Chem Chem Phys, 2019, 21: 4258–4267
Gaines E, Maisuria K, Di Tommaso D. CrystEngComm, 2016, 18: 2937–2948
Ectors P, Duchstein P, Zahn D. Cryst Growth Des, 2014, 14: 2972–2976
Di Tommaso D. CrystEngComm, 2013, 15: 6564–6577
Parveen S, Davey RJ, Dent G, Pritchard RG. Chem Commun, 2005, 12: 1531–1533
Chen J, Trout BL. J Phys Chem B, 2008, 112: 7794–7802
Rosbottom I, Toroz D, Hammond RB, Roberts KJ. CrystEngComm, 2018, 20: 7543–7555
Tang W, Mo H, Zhang M, Gong J, Wang J, Li T. Cryst Growth Des, 2017, 17: 5028–5033
Tang W, Zhang M, Mo H, Gong J, Wang J, Li T. Cryst Growth Des, 2017, 17: 5049–5053
Gaines E, Di Tommaso D. Pharmaceutics, 2018, 10: 12
Davey RJ, Blagden N, Righini S, Alison H, Quayle MJ, Fuller S. Cryst Growth Des, 2001, 1: 59–65
Hunter CA, McCabe JF, Spitaleri A. CrystEngComm, 2012, 14: 7115–7117
Chiarella RA, Gillon AL, Burton RC, Davey RJ, Sadiq G, Auffret A, Cioffi M, Hunter CA. Faraday Discuss, 2007, 136: 179–193
Chadwick K, Davey RJ, Dent G, Pritchard RG, Hunter CA, Musumeci D. Cryst Growth Des, 2009, 9: 1990–1999
Zong S, Wang J, Wu H, Liu Q, Hao Y, Huang X, Wu D, Zhou G, Hao H. Acta Crystlogr B Struct Sci Cryst Eng Mater, 2019, 75: 845–854
Svärd M, Rasmuson ÅC. Cryst Growth Des, 2013, 13: 1140–1152
Davey RJ, Dent G, Mughal RK, Parveen S. Cryst Growth Des, 2006, 6: 1788–1796
Hylton RK, Tizzard GJ, Threlfall TL, Ellis AL, Coles SJ, Seaton CC, Schulze E, Lorenz H, Seidel-Morgenstern A, Stein M, Price SL. J Am Chem Soc, 2015, 137: 11095–11104
Du W, Bai L, Gong Y, Zhang L, Xiang J, Wang S, Tang N, Zhu L, Yin Q. Ind Eng Chem Res, 2019, 58: 23284–23293
Hansen TB, Taris A, Rong BG, Grosso M, Qu H. J Cryst Growth, 2016, 450: 81–90
Su W, Zhang Y, Liu J, Ma M, Guo P, Liu X, Wang H, Li C. J Pharmaceutical Sci, 2020, 109: 1537–1546
Liu S, Xu S, Tang W, Yu B, Hou B, Gong J. CrystEngComm, 2018, 20: 7435–7445
Mattei A, Li T. Pharm Res, 2012, 29: 460–470
Du W, Cruz-Cabeza AJ, Woutersen S, Davey RJ, Yin Q. Chem Sci, 2015, 6: 3515–3524
Tang W, Mo H, Zhang M, Parkin S, Gong J, Wang J, Li T. J Phys Chem B, 2017, 121: 10118–10124
Maggioni GM, Bezinge L, Mazzotti M. Cryst Growth Des, 2017, 17: 6703–6711
Jones CD, Walker M, Xiao Y, Edkins K. Chem Commun, 2019, 55: 4865–4868
Wu X, Zheng S, Zhang J, Li W. CrystEngComm, 2019, 21: 3209–3217
Sullivan RA, Davey RJ, Sadiq G, Dent G, Back KR, ter Horst JH, Toroz D, Hammond RB. Cryst Growth Des, 2014, 14: 2689–2696
Mealey D, Zeglinski J, Khamar D, Rasmuson ÅC. Faraday Discuss, 2015, 179: 309–328
Chai Y, Wang L, Bao Y, Teng R, Liu Y, Xie C. Cryst Growth Des, 2019, 19: 1660–1667
Lynch MB, Lawrence SE, Nolan M. J Phys Chem A, 2018, 122: 3301–3312
Zeglinski J, Kuhs M, Khamar D, Hegarty AC, Devi RK, Rasmuson ÅC. Chem Eur J, 2018, 24: 4916–4926
Zeglinski J, Kuhs M, Devi KR, Khamar D, Hegarty AC, Thompson D, Rasmuson ÅC. Cryst Growth Des, 2019, 19: 2037–2049
Liu Y, Xu S, Zhang X, Tang W, Gong J. Cryst Growth Des, 2019, 19: 7175–7184
Rexrode NR, Orien J, King MD. J Phys Chem A, 2019, 123: 6937–6947
Cruz-Cabeza AJ, Davey RJ, Sachithananthan SS, Smith R, Tang SK, Vetter T, Xiao Y. Chem Commun, 2017, 53: 7905–7908
Tang SK, Davey RJ, Sacchi P, Cruz-Cabeza AJ. Chem Sci, 2021, 12: 993–1000
Uzoh OG, Cruz-Cabeza AJ, Price SL. Cryst Growth Des, 2012, 12: 4230–4239
Cruz-Cabeza AJ, Liebeschuetz JW, Allen FH. CrystEngComm, 2012, 14: 6797–6811
Klitou P, Rosbottom I, Simone E. Cryst Growth Des, 2019, 19: 4774–4783
Puglisi A, Giovannini T, Antonov L, Cappelli C. Phys Chem Chem Phys, 2019, 21: 15504–15514
Luchian R, Vinţeler E, Chiş C, Vasilescu M, Leopold N, Prates Ramalho JP, Chiş V. J Pharmaceutical Sci, 2017, 106: 3564–3573
Li P, Hwang J, Maier JM, Zhao C, Kaborda DV, Smith MD, Pellechia PJ, Shimizu KD. Cryst Growth Des, 2015, 15: 3561–3564
Baker CM, Grant GH. Chem Commun, 2006, 13: 1387–1389
Merrill AT, Tantillo DJ. Magn Reson Chem, 2020, 58: 576–583
Shaikh SR, Gawade RL, Kumar D, Kotmale A, Gonnade RG, Stürzer T. Cryst Growth Des, 2019, 19: 5665–5678
Francisco CB, Fernandes CS, de Melo UZ, Rittner R, Gauze GF, Basso EA. Beilstein J Org Chem, 2019, 15: 818–829
Levi G, Biasin E, Dohn AO, Jónsson H. Phys Chem Chem Phys, 2020, 22: 748–757
Quesada-Moreno MM, Cruz-Cabeza AJ, Avilés-Moreno JR, Cabildo P, Claramunt RM, Alkorta I, Elguero J, Zúñiga FJ, López-González JJ. J Phys Chem A, 2017, 121: 5665–5674
Vojta GM, Etter MC. Cheminform, 1990, 7: 3–11
Thureau P, Carvin I, Ziarelli F, Viel S, Mollica G. Angew Chem Int Ed, 2019, 58: 16047–16051
Tang N, Wang X, Du W, Zhang L, Xiang J, Wang S, Cheng P, Zhu L, Yin Q. Cryst Growth Des, 2019, 19: 2050–2059
Back KR, Davey RJ, Grecu T, Hunter CA, Taylor LS. Cryst Growth Des, 2012, 12: 6110–6117
Kessler H, Zimmermann G, Förster H, Engel J, Oepen G, Sheldrick WS. Angew Chem Int Ed, 1981, 20: 1053–1055
Shi P, Xu S, Du S, Rohani S, Liu S, Tang W, Jia L, Wang J, Gong J. Cryst Growth Des, 2018, 18: 5947–5956
Li X, Wang N, Yang J, Huang Y, Ji X, Huang X, Wang T, Wang H, Hao H. IUCrJ, 2020, 7: 542–556
Gawade RL, Chakravarty DK, Kotmale A, Sangtani E, Joshi PV, Ahmed A, Mane MV, Das S, Vanka K, Rajamohanan PR, Puranik VG, Gonnade RG. Cryst Growth Des, 2016, 16: 2416–2428
Cruz-Cabeza AJ. Acta Crystlogr B Struct Sci Cryst Eng Mater, 2016, 72: 437–438
Adjiman CS, Brandenburg JG, Braun DE, Cole J, Collins C, Cooper AI, Cruz-Cabeza AJ, Day GM, Dudek M, Hare A, Iuzzolino L, McKay D, Mitchell JBO, Mohamed S, Neelamraju S, Neumann M, Nilsson Lill S, Nyman J, Oganov AR, Price SL, Pulido A, Reutzel-Edens S, Rietveld I, Ruggiero MT, Schön JC, Tsuzuki S, van den Ende J, Woollam G, Zhu Q. Faraday Discuss, 2018, 211: 493–539
Cruz-Cabeza AJ, Davey RJ, Oswald IDH, Ward MR, Sugden IJ. CrystEngComm, 2019, 21: 2034–2042
Yu L, Reutzel-Edens SM, Mitchell CA. Org Process Res Dev, 2000, 4: 396–402
Greenwell C, McKinley JL, Zhang P, Zeng Q, Sun G, Li B, Wen S, Beran GJO. Chem Sci, 2020, 11: 2200–2214
Derdour L, Skliar D. Chem Eng Sci, 2014, 106: 275–292
Tang W, Sima AD, Gong J, Wang J, Li T. Cryst Growth Des, 2020, 20: 1779–1788
Roy S, Banerjee R, Nangia A, Kruger GJ. Chem Eur J, 2006, 12: 3777–3788
Goldstein RI, Guo R, Hughes C, Maurer DP, Newhouse TR, Sisto TJ, Conry RR, Price SL, Thamattoor DM. CrystEngComm, 2015, 17: 4877–4882
Lemmerer A, Báthori NB, Esterhuysen C, Bourne SA, Caira MR. Cryst Growth Des, 2009, 9: 2646–2655
Yu L, Stephenson GA, Mitchell CA, Bunnell CA, Snorek SV, Bowyer JJ, Borchardt TB, Stowell JG, Byrn SR. J Am Chem Soc, 2000, 122: 585–591
Threlfall TL, De’Ath RW, Coles SJ. Org Process Res Dev, 2013, 17: 578–584
Derdour L, Skliar D. Cryst Growth Des, 2012, 12: 5180–5187
Derdour L, Pack SK, Skliar D, Lai CJ, Kiang S. Chem Eng Sci, 2011, 66: 88–102
Derdour L, Sivakumar C, Skliar D, Pack SK, Lai CJ, Vernille JP, Kiang S. Cryst Growth Des, 2012, 12: 5188–5196
Derdour L, Chan EJ. AIChE J, 2015, 61: 4456–4469
Derdour L, Chan EJ, Skliar D. Processes, 2019, 7: 611
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This work was supported by the National Natural Science Foundation of China (21978201).
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Li, X., Wang, J., Wang, T. et al. Molecular mechanism of crystal nucleation from solution. Sci. China Chem. 64, 1460–1481 (2021). https://doi.org/10.1007/s11426-021-1015-9
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DOI: https://doi.org/10.1007/s11426-021-1015-9