有机晶体成核分子机理研究进展

摘要

溶液成核是影响晶体材料的理性设计与精准制备的关键过程，因而对于晶体成核的机理理解从而实现精准控制至关重要。晶体成核研究历经了几个世纪的发展，形成了经典成核理论与非经典成核机理2种主流学说。综述了近年来晶体成核分子机理方面的研究进展，首先简介了经典成核理论的发展及问题，重点介绍了溶液化学、多晶型及晶体成核的分子机理，引出了两步成核与成核团簇前驱体2种典型的非经典机理，总结了成核机理与控制在晶体设计中的应用。最后，对成核分子机理研究方面进行了总结与展望。

	Service

	把本文推荐给朋友
	加入我的书架
	加入引用管理器
	Email Alert
	RSS
	作者相关文章
	汤伟伟
	李斯
	龚俊波

关键词：成核；多晶型；溶液化学

Abstract：

Crystal nucleation from solution is a key process for the rational design and precise production of the desired structure and properties of crystalline materials. Understanding of crystal nucleation mechanism and hence the precise control is of fundamental importance. Crystal nucleation was studied for several centuries, and two main schools of thought, classic nucleation theory and non-classic nucleation mechanism, were proposed. The review summarized the research progress in recent years on molecular mechanism of crystal nucleation from solution. It was briefly introduced the development and problem of classic nucleation theory. Recent studies on solution chemistry, polymorphic formation and crystal nucleation mechanism were reviewed in detail. Two-step mechanism and pre-nucleation cluster pathway were then introduced, and the application of understanding and control of crystal nucleation was summarized. Finally, the future study on crystal nucleation mechanism was discussed and outlooked.

Keywords： crystal nucleation； polymorphism； solution chemistry

Received 2018-04-15;

Fund:

国家自然科学基金创新研究群体项目（21621004）和国家科技重大专项（2017ZX09101001）。

Corresponding Authors: 龚俊波,E-mail:junbo_gong@tju.edu.cn。 Email: junbo_gong@tju.edu.cn

About author: 汤伟伟(1988-),男,博士,讲师,现从事工业结晶科学与技术领域研究。

引用本文:

汤伟伟, 李斯, 龚俊波.有机晶体成核分子机理研究进展[J]. 化学工业与工程, 2018,35(3): 2-11

Tang Weiwei, Li Si, Gong Junbo.Research Progress on Molecular Mechanism of Nucleation of Organic Crystals[J]. Chemcial Industry and Engineering, 2018,35(3): 2-11

[1] Khamar D, Zeglinski J, Mealey D, et al. Investigating the role of solvent-solute interaction in crystal nucleation of salicylic acid from organic solvents[J]. Journal of the American Chemical Society, 2014, 136(33):11664-11673
[2] Chattopadhyay S, Erdemir D, Evans J M B, et al. SAXS study of the nucleation of glycine crystals from a supersaturated solution[J]. Crystal Growth & Design, 2005, 5(2):523-527
[3] Jackson R N, Golden S M, van Erp P B G, et al. Crystal structure of the CRISPR RNA-guided surveillance complex from Escherichia coli[J]. Science, 2014, 345(6203):1473-1479
[4] Mulepati S, Heroux A, Bailey S. Crystal structure of a CRISPR RNA-guided surveillance complex bound to a ssDNA target[J]. Science, 2014, 345(6203):1479-1484
[5] Zhao S, Gong P, Luo S, et al. Beryllium-Free Rb3Al3B3O10F with reinforced inter layer bonding as a deep-ultraviolet nonlinear optical crystal[J]. Journal of the American Chemical Society, 2015,137(6):2207-2210
[6] Schiotz J, DiTolla F D, Jacobsen K W. Softening of nanocrystalline metals at very small grain sizes[J]. Nature, 1998, 391(6667):561-563
[7] Mullin J W. Crystallization[M]. Oxford:Butterworth-Heinemann, 2001
[8] Davey R J, Schroeder S L M, ter Horst J H. Nucleation of organic crystalsa molecular perspective[J]. Angewandte Chemie-International Edition, 2013, 52(8):2166-2179
[9] Kelton K F, Frenkel D. Preface:Special topic on nucleation:New concepts and discoveries[J]. Journal of Chemical Physics, 2016, 145(21):211501
[10] Davey R J, Garside J. From molecules to crystallizers[M]. Oxford:Butterworth-Heinemann,2000
[11] Kashchiev D. Nucleation:Basic theory with applications[M]. Oxford:Butterworth-Heinemann, 2000
[12] Kashchiev D, van Rosmalen G M. Review:Nucleation in solutions revisited[J]. Crystal Resesrch Technology, 2003, 38(7/8):555-574
[13] Davey R J, Schroeder S L, ter Horst J H. Nucleation of organic crystals-A molecular perspective[J]. Angewandte Chemie-International Edition, 2013, 52(8):2166-2179
[14] Sharaf M A, Dobbins R A. A comparison of measured nucleation rates with the predictions of several theories of homogeneous nucleation[J]. Journal of Chemical Physics, 1982, 77(3):1517-1526
[15] Strey R, Wagner P E, Schmeling T. Homogeneous nucleation rates for n-alcohol vapors measured in a two-piston expansion chamber[J]. Chemischer Informationsdienst, 1986, 17(27):2325-2335
[16] Bernstein J, Davey R J, Henck J O. Concomitant polymorphs[J]. Angewandte Chemie International Edition, 1999, 38(23):3440-3461
[17] Desiraju G R. Crystal engineering:Outlook and prospects[J]. Currentence, 2001, 81(8):1038-1042
[18] Erdemir D, Lee A Y, Myerson A S. Nucleation of crystals from solution:Classical and two-step models[J]. Accounts of Chemical Research, 2009, 42(5):621-629
[19] Gebauer D, Kellermeier M, Gale J D, et al. Pre-Nucleation clusters as solute precursors in crystallisation[J]. Chemical Society Reviews, 2014, 43(7):2348-2371
[20] Gebauer D, Völkel A, Cölfen H. Stable prenucleation calcium carbonate clusters[J]. Science, 2008, 322(5909):1819-1822
[21] Myerson A S, Trout B L. Nucleation from solution[J]. Science, 2013, 341(6148):855-856
[22] Vekilov P G. Nucleation[J]. Crystal Growth & Design, 2010,10(12):5007-5019
[23] McCrone W C. Polymorphism[J]. Physics and chemistry of the organic solid state, 1965, 2:725-767
[24] Byrn S R, Pfeiffer R R, Stowell J G. Solid-State chemistry of drugs[J]. Indiana:SSCI Inc, 1999
[25] Brittain H G. Polymorphism in pharmaceutical solids[M]. New York:CRC Press, 2009
[26] Peschar R, Pop M M, De Ridder D J A, et al. Crystal structures of 1,3-distearoyl-2-oleoylglycerol and cocoa butter in the β(V) phase reveal the driving force behind the occurrence of fat bloom on chocolate[J]. Journal of Physical Chemistry B, 2004, 108(40):15450-15453
[27] Cruz-Cabeza A J, Bernstein J. Conformational polymorphism[J]. Chemical Reviews, 2014, 114(4):2170-2191
[28] Liebig J, Wohler F. Untersuchungen iiber das Radical der Benzoesaure[J]. Pharm Anntiinflam, 1832, 249:514
[29] David W I F, Shankland K, Pulham C R, et al. Polymorphism in benzamide[J]. Angewandte Chemie-International Edition, 2005, 44(43):7032-7035
[30] Etter M C. Hydrogen bonds as design elements in organic chemistry[J]. Journal of Physical Chemistry B, 1991, 95(12):4601-4610
[31] Weissbuch I, Meir Lahav A, Leiserowitz L. Toward stereochemical control, monitoring, and understanding of crystal nucleation[J]. Crystal Growth & Design, 2003, 3(2):125-150
[32] Davey R J, Blagden N, Righini S, et al. Crystal polymorphism as a probe for molecular self-assembly during nucleation from solutions:The case of 2,6-dihydroxybenzoic acid[J]. Crystal Growth & Design, 2001, 1(1):59-65
[33] Parveen S, Davey R J, Dent G, et al. Linking solution chemistry to crystal nucleation:The case of tetrolic acid[J]. Chemical Communications, 2005, 12(12):1531
[34] Hunter C A, McCabe J F, Spitaleri A. Solvent effects of the structures of prenucleation aggregates of carbamazepine[J]. Cryst Eng Comm, 2012, 14(21):7115-7117
[35] Spitaleri A, Hunter C A, Mccabe J F, et al. A ¹H NMR study of crystal nucleation in solution[J]. Crystal Engineering Communication, 2004, 6(80):489-493
[36] Chiarella R A, Gillon A L, Burton R C, et al. The nucleation of inosine:The impact of solution chemistry on the appearance of polymorphic and hydrated crystal forms[J]. Faraday Discussions, 2007, 136(1):179-193
[37] Kulkarni S A, Mcgarrity E S, Meekes H, et al. Isonicotinamide self-association:The link between solvent and polymorph nucleation[J]. Chemical Communications, 2012, 48(41):4983-4985
[38] Tang W, Mo H, Zhang M, et al. Persistent self-association of solute molecules in solution[J]. Journal of Physical Chemistry B, 2017, 121(43):10118-10124
[39] Chang Y, Myerson A S. Diffusivity of glycine in concentrated saturated and supersaturated aqueous solutions[J]. AIChE J, 1986, 32(9):1567-1569
[40] Myerson A S, Lo P Y. Diffusion and cluster formation in supersaturated solutions[J]. Journal of Crystal Growth, 1990, 99(1/4):1048-1052
[41] Gidalevitz D, Feidenhans'l R, Matlis S, et al. Monitoring in situ growth and dissolution of molecular crystals:Towards determination of the growth units[J]. Angewandte Chemie-International Edition, 1997, 36(9):955-959
[42] Huang J, Stringfellow T C, Yu L. Glycine exists mainly as monomers, not dimers, in supersaturated aqueous solutions:Implications for understanding its crystallization and polymorphism[J]. Journal of the American Chemical Society, 2008, 130(42):13973-13980
[43] Tang W, Mo H, Zhang M, et al. Glycine's pH-dependent polymorphism:A perspective from self-association in solution[J]. Crystal Growth & Design, 2017,17(10):5028-5033
[44] Tang W, Zhang M, Mo H, et al. Higher-Order self-assembly of benzoic acid in solution[J]. Crystal Growth & Design,2017, 17(10):5049-5053
[45] Threlfall T. Crystallisation of polymorphs:Thermodynamic insight into the role of solvent[J]. Organic Process Research & Development, 2000, 4(5):384-390
[46] Lahav M, Leiserowitz L. The effect of solvent on crystal growth and morphology[J]. Chemical Engineering Science, 2001, 56(7):2245-2253
[47] Long S, Parkin S, Siegler M A, et al. Polymorphism and phase behaviors of 2-(phenylamino)nicotinic acid[J]. Crystal Growth & Design, 2008, 8(11):4006-4013
[48] Wallace A F, Hedges L O, Fernandezmartinez A, et al. Microscopic evidence for liquid-liquid separation in supersaturated CaCO₃ solutions[J]. Science, 2013, 341(6148):885-889
[49] Shore J D, Perchak D, Shnidman Y. Simulations of the nucleation of AgBr from solution[J]. Journal of Chemical Physics, 2000, 113(15):6276-6284
[50] Vekilov P G. Dense liquid precursor for the nucleation of ordered solid phases from solution[J]. Crystal Growth & Design, 2004, 4(4):671-685
[51] Galkin O, Pan W, Filobelo L, et al. Two-Step mechanism of homogeneous nucleation of sickle cell hemoglobin polymers[J]. Biophysical Journal, 2007, 93(3):902-913
[52] Asherie N, Lomakin A, Benedek G B. Phase diagram of colloidal solutions[J]. Physical Review Letters, 1996, 77(23):4832-4835
[53] Sommerdijk N A J M, With G D. Biomimetic CaCO₃ mineralization using designer molecules and interfaces[J]. Chemical Reviews, 2008, 108(11):4499-4550
[54] Garetz B A, Matic J, Myerson A S. Polarization switching of crystal structure in the nonphotochemical light-induced nucleation of supersaturated aqueous glycine solutions[J]. Physical Review Letters, 2002, 89(17):175501
[55] Pan W, Kolomeisky A B, Vekilov P G. Nucleation of ordered solid phases of proteins via a disordered high-density state:Phenomenological approach[J]. The Journal of Chemical Physics, 2005, 122(17):174905
[56] Chen J, Sarma B, Evans J M B, et al. Pharmaceutical crystallization[J]. Crystal Growth & Design, 2011, 11(4):887-895
[57] Betts F, Posner A S. An X-ray radial distribution study of amorphous calcium phosphate[J]. Materials Research Bulletin, 1974, 9(3):353-360
[58] And K O, Atsuo I. Cluster growth model for hydroxyapatite[J]. Chemistry of Materials, 1998, 10(11):3346-3351
[59] Gebauer D, Cölfen H. Prenucleation clusters and non-classical nucleation[J]. Nano Today, 2011, 6(6):564-584
[60] Desiraju G R. Supramolecular synthons in crystal engineering-A new organic synthesis[J]. Angewandte Chemie International Edition, 1995, 34(21):2311-2327
[61] Duggirala N K, Perry M L, Almarsson O, et al. Pharmaceutical cocrystals:Along the path to improved medicines[J]. Chemical Communications, 2016, 52(4):640-655
[62] Qiao N, Li M, Schlindwein W, et al. Pharmaceutical cocrystals:An overview[J]. International journal of pharmaceutics, 2011, 419(1):1-11
[63] Dunitz J D, Gavezzotti A. Supramolecular synthons:Validation and ranking of intermolecular interaction energies[J]. Crystal Growth & Design, 2012, 12(12):5873-5877
[64] Aakeröy C B, Baldrighi M, Desper J, et al. Supramolecular hierarchy among halogen-bond donors[J]. Chemistry, 2013, 19(48):16240-16247
[65] Aakeröy C B, Epa K N, Forbes S, et al. Competing hydrogen-bond donors:Phenols vs. cyanooximes[J]. Cryst Eng Comm, 2013, 15(30):5946-5949
[66] Gavezzotti A. Molecular aggregation of acetic acid in a carbon tetrachloride solution:A molecular dynamics study with a view to crystal nucleation[J]. Chemistry-A European Journal, 1999, 5(2):567-576
[67] Gavezzotti A, Filippini G, Kroon J, et al. The crystal polymorphism of tetrolic acid (CH₃C-CCOOH):A molecular dynamics study of precursors in solution, and a crystal structure generation[J] Chemistry-A European Journal, 1997, 3(6):893-899
[68] Bernstein J. Polymorphism in molecular crystals[M]. Oxford University Press, 2008
[69] Reeves L W. Studies of hydrogen bonding in carboxylic acids[J]. Transactions of the Faraday Society, 1959, 55:1684-1688
[70] Gavezzotti A, Filippini G. Geometry of the intermolecular X-H…Y (X, Y=N, O) hydrogen bond and the calibration of empirical hydrogen-bond potentials[J]. Journal of Physical Chemistry, 1994, 98(18):4831-4837
[71] Bernstein J, Davis R E, Shimoni L, et al. Patterns in hydrogen bonding:Functionality and graph set analysis in crystals[J]. Angewandte Chemie International Edition, 1995, 34(15):1555-1573
[72] Kulkarni S, McGarrity E, Meeks H, et al. Isonicotinamide self-association:The link between solvent and polymorph nucleation[J]. Chemical Communications, 2012, 48(41):4983-4985
[73] Parveen S, Davey R, Dent G, et al. Linking solution chemistry to crystal nucleation:the case of tetrolic acid[J]. Chemical Communications, 2005, (12):1531-1533