Synlett 2016; 27(13): 1907-1918
DOI: 10.1055/s-0035-1561448
account
© Georg Thieme Verlag Stuttgart · New York

Organic Molecules with Porous Crystal Structures

Mohamed I. Hashim
University of Houston, Department of Chemistry, 3585 Cullen Boulevard #112, Houston TX 77204-5003, USA   URL: miljanicgroup.com   Email: miljanic@uh.edu
,
Chia-Wei Hsu
University of Houston, Department of Chemistry, 3585 Cullen Boulevard #112, Houston TX 77204-5003, USA   URL: miljanicgroup.com   Email: miljanic@uh.edu
,
Ha T. M. Le
University of Houston, Department of Chemistry, 3585 Cullen Boulevard #112, Houston TX 77204-5003, USA   URL: miljanicgroup.com   Email: miljanic@uh.edu
,
Ognjen Š. Miljanić*
University of Houston, Department of Chemistry, 3585 Cullen Boulevard #112, Houston TX 77204-5003, USA   URL: miljanicgroup.com   Email: miljanic@uh.edu
› Author Affiliations
Further Information

Publication History

Received: 19 February 2016

Accepted after revision: 24 March 2016

Publication Date:
18 May 2016 (online)


Abstract

Porous materials have numerous applications of relevance to energy, the environment, and catalysis. A relatively recent addition to the field are porous molecular crystals, whose solid-state structures contain discrete molecules held together only by weak noncovalent forces. This contribution summarizes recent developments in the area, before providing an account of our own adventures in the field which are centered on the creation of robust fluorinated porous molecular crystals. We will also present the recent discovery of a one-step synthesis of a new class of macrocycles dubbed cyclobenzoins; an example is given of such a shape-persistent structure that translates into mild porosity in the solid state.

1 Introduction

2 Early Days

3 Intrinsically Porous Molecular Crystals

4 Extrinsically Porous Molecular Crystals

5 Fluorinated Porous Molecular Crystals

6 Cyclobenzoins: Shape-Persistent and Intrinsically Porous?

7 Conclusions

 
  • References

  • 1 Schüth F, Sing KS. W, Weitkamp J. Handbook of Porous Solids . John Wiley and Sons; Hoboken, NJ: 2002
  • 2 Slater AG, Cooper AI. Science 2015; 348: aaa8075-1
  • 3 Beaudoin D, Maris T, Wuest JD. Nat. Chem. 2013; 5: 830
  • 4 Holst JR, Trewin A, Cooper AI. Nat. Chem. 2010; 2: 915
  • 5 McKeown NB. J. Mater. Chem. 2010; 20: 10588
  • 6 Tian J, Thallapally PK, McGrail BP. CrystEngComm 2012; 14: 1909
  • 7 Barbour LJ. Chem. Commun. (Cambridge) 2006; 1163
  • 8 Tranchemontagne DJ, Ni Z, O’Keeffe M, Yaghi OM. Angew. Chem. Int. Ed. 2008; 47: 5136
  • 9 Dianin J. J. Russ. Phys. Chem. Soc. 1914; 46: 1310
  • 10 Barrer RM, Shanson VH. J. Chem. Soc., Chem. Commun. 1976; 333
  • 11 Atwood JL, Barbour LJ, Jerga A, Schottel BL. Science 2002; 298: 1000
  • 12 Sozzani P, Bracco S, Comotti A, Ferretti L, Simonutti R. Angew. Chem. Int. Ed. 2005; 44: 1816
  • 13 Görbitz CH. Chem. Eur. J. 2007; 13: 1022
  • 14 Soldatov DV, Moudrakovski IL, Ripmeester JA. Angew. Chem. Int. Ed. 2004; 43: 6308
  • 15 Soldatov DV, Moudrakovski IL, Grachev EV, Ripmeester JA. J. Am. Chem. Soc. 2006; 128: 6737
  • 16 Shimizu LS, Hughes AD, Smith MD, Davis MJ, Zhang BP, zur Loye HC, Shimizu KD. J. Am. Chem. Soc. 2003; 125: 14972
  • 17 Dewal MB, Lufaso MW, Hughes AD, Samuel SA, Pellechia P, Shimizu LS. Chem. Mater. 2006; 18: 4855
  • 18 Xu Y, Smith MD, Geer MF, Pellechia PJ, Brown JC, Wibowo AC, Shimizu LS. J. Am. Chem. Soc. 2010; 132: 5334
  • 19 Shimizu LS, Salpage SR, Korous AA. Acc. Chem. Res. 2014; 47: 2116
  • 20 Natarajan R, Bridgland L, Sirikulajorn A, Lee J.-H, Haddow MF, Magro G, Ali B, Narayanan S, Strickland P, Charmant JP. H, Orpen AG, McKeown NB, Bezzu CG, Davis AP. J. Am. Chem. Soc. 2013; 135: 16912
  • 21 Msayib KJ, Book D, Budd PM, Chaukura N, Harris KD. M, Helliwell M, Tedds S, Walton A, Warren JE, Xu M, McKeown NB. Angew. Chem. Int. Ed. 2009; 48: 3273
  • 22 Evans JD, Huang DM, Haranczyk M, Thornton AW, Sumby CJ, Doonan CJ. CrystEngComm 2016; DOI: 10.1039/c6ce00064a
  • 23 For a review of imine-based porous materials, including COFs and organic cages, see: Jin Y, Zhu Y, Zhang W. CrystEngComm 2013; 15: 1484
  • 24 Tozawa T, Jones JT. A, Swamy SI, Jiang S, Adams DJ, Shakespeare S, Clowes R, Bradshwa D, Hasell T, Chong SY, Tang C, Thompson S, Parker J, Trewin A, Bacsa J, Slawin AM. Z, Steiner A, Cooper AI. Nat. Mater. 2009; 8: 973
  • 25 Mitra T, Wu X, Clowes R, Jones JT. A, Jelfs KE, Adams DJ, Trewin A, Bacsa J, Steiner A, Cooper AI. Chem. Eur. J. 2011; 17: 10235
  • 26 Jones JT. A, Holden D, Mitra T, Hasell T, Adams DJ, Jelfs KE, Trewin A, Willock DJ, Day GM, Bacsa J, Steiner A, Cooper AI. Angew. Chem. Int. Ed. 2011; 50: 749
  • 27 Culshaw JL, Cheng G, Schmidtmann M, Hasell T, Liu M, Adams DJ, Cooper AI. J. Am. Chem. Soc. 2013; 135: 10007
  • 28 Hasell T, Schmidtmann M, Cooper AI. J. Am. Chem. Soc. 2011; 133: 14920
  • 29 Jones JT. A, Hasell T, Wu X, Bacsa J, Jelfs KE, Schmidtmann M, Chong SY, Adams DJ, Trewin A, Schiffman F, Cora F, Slater B, Steiner A, Day GM, Cooper AI. Nature 2011; 474: 367
  • 30 Hasell T, Chong SY, Schmidtmann M, Adams DJ, Cooper AI. Angew. Chem. Int. Ed. 2012; 51: 7154
  • 31 Jiang S, Bacsa J, Wu X, Jones JT. A, Dawson R, Trewin A, Adams DJ, Cooper AI. Chem. Commun. 2011; 47: 8919
  • 32 Jelfs KE, Wu X, Schmidtmann M, Jones JT. A, Warren JE, Adams DJ, Cooper AI. Angew. Chem. Int. Ed. 2011; 50: 10653
  • 33 Giri N, Davidson CE, Melaugh G, Del Pópolo MG, Jones JT. A, Hasell T, Cooper AI, Horton PN, Hursthouse MB, James SL. Chem. Sci. 2012; 3: 2153
  • 34 Giri N, Del Pópolo MG, Melaugh G, Greenaway RL, Rätzke K, Koschine T, Pison L, Costa Gomes MF, Cooper AI, James SL. Nature 2015; 527: 216
  • 35 Mastalerz M. Chem. Commun. (Cambridge) 2008; 4756
  • 36 Mastalerz M, Schneider MW, Oppel IM, Presly O. Angew. Chem. Int. Ed. 2011; 50: 1046
  • 37 Schneider MW, Oppel IM, Ott H, Lechner LG, Hauswald H.-JS, Stoll R, Mastalerz M. Chem. Eur. J. 2012; 18: 836
  • 38 Brutschy M, Schneider MW, Mastalerz M, Waldvogel SR. Adv. Mater. 2012; 24: 6049
  • 39 Brutschy M, Schneider MW, Mastalerz M, Waldvogel SR. Chem. Commun. 2013; 49: 8398
  • 40 Elbert SM, Rominger F, Mastalerz M. Chem. Eur. J. 2014; 20: 16707
  • 41 Mastalerz M. Synlett 2013; 24: 781
  • 42 Jin YH, Voss BA, Jin A, Long H, Noble RD, Zhang W. J. Am. Chem. Soc. 2011; 133: 6650
  • 43 Côté AP, Benin AI, Ockwig NW, O’Keeffe M, Matzger AJ, Yaghi OM. Science 2005; 310: 1166
  • 44 Zhang G, Presly O, White F, Oppel IM, Mastalerz M. Angew. Chem. Int. Ed. 2014; 53: 1516
  • 45 Zhang G, Presly O, White F, Oppel IM, Mastalerz M. Angew. Chem. Int. Ed. 2014; 53: 5126
  • 46 Mastalerz M, Oppel IM. Angew. Chem. Int. Ed. 2012; 51: 5252
  • 47 Kohl B, Rominger F, Mastalerz M. Org. Lett. 2014; 16: 704
  • 48 Kohl B, Rominger F, Mastalerz M. Chem. Eur. J. 2015; 21: 17308
  • 49 Taylor RG. D, Carta M, Bezzu CG, Walker J, Msayib KJ, Kariuki BM, McKeown NB. Org. Lett. 2014; 16: 1848
  • 50 He Y, Xiang S, Chen B. J. Am. Chem. Soc. 2011; 133: 14570
  • 51 Brunet P, Simard M, Wuest JD. J. Am. Chem. Soc. 1997; 119: 2737
  • 52 Li P, He Y, Arman HD, Krishna R, Wang H, Weng L, Chen B. Chem. Commun. 2014; 50: 13081
  • 53 Li P, He Y, Guang J, Weng L, Zhao JC.-G, Xiang S, Chen B. J. Am. Chem. Soc. 2014; 136: 547
  • 54 Li P, He Y, Zhao Y, Weng L, Wang H, Krishna R, Wu H, Zhou W, O’Keeffe M, Han Y, Chen B. Angew. Chem. Int. Ed. 2015; 54: 574
  • 55 Wang H, Li B, Wu H, Hu T.-L, Yao Z, Zhou W, Xiang S, Chen B. J. Am. Chem. Soc. 2015; 137: 9963
  • 56 Yang W, Li B, Wang H, Alduhaish O, Alfooty K, Zayed MA, Li P, Arman HD, Chen B. Cryst. Growth Des. 2015; 15: 2000
  • 57 Chen T.-H, Popov I, Zenasni O, Daugulis O, Miljanić OŠ. Chem. Commun. 2013; 49: 6846
  • 58 Chen T.-H, Popov I, Kaveevivitchai W, Chuang Y.-C, Chen Y.-S, Jacobson AJ, Miljanić OŠ. Angew. Chem. Int. Ed. 2015; 54: 13902
  • 59 Padial NM, Procopio EQ, Montoro C, López E, Oltra JE, Colombo V, Maspero A, Masciocchi N, Galli S, Senkovska I, Kaskel S, Barea E, Navarro JA. R. Angew. Chem. Int. Ed. 2013; 52: 8290
  • 60 Chen T.-H, Popov I, Kaveevivitchai W, Chuang Y.-C, Chen Y.-S, Daugulis O, Jacobson AJ, Miljanić OŠ. Nat. Commun. 2014; 5 DOI: 10.1038/ncomms6131
  • 61 Chen T.-H, Kaveevivitchai W, Jacobson AJ, Miljanić OŠ. Chem. Commun. 2015; 51: 14096
  • 62 Hendon C, Wittering K, Chen T.-H, Kaveevivitchai W, Popov I, Butler KT, Wilson CC, Cruickshank D, Miljanić OŠ, Walsh A. Nano Lett. 2015; 15: 2149
  • 63 Ji Q, Lirag RC, Miljanić OŠ. Chem. Soc. Rev. 2014; 43: 1873
    • 64a Grimaux E. C. R. Hebd. Seances Acad. Sci. 1876; 83: 826
    • 64b Oppenheimer H. Ber. Dtsch. Chem. Ges. 1886; 19: 1814
    • 64c Jones JI, Tinker PB. J. Chem. Soc. 1955; 1286
  • 65 Ji Q, Le HT. M, Wang X, Chen Y.-S, Makarenko T, Jacobson AJ, Miljanić OŠ. Chem. Eur. J. 2015; 21: 17205
  • 66 Ji Q, Do LH, Miljanić OŠ. Synlett 2015; 26: 1625
  • 67 Hasell T, Culshaw JL, Chong SY, Schmidtmann M, Little MA, Jelfs KE, Pyzer-Knapp EO, Shepherd H, Adams DJ, Day GM, Cooper AI. J. Am. Chem. Soc. 2014; 136: 1438
  • 68 Tanabe KK, Cohen SM. Chem. Soc. Rev. 2011; 40: 498