10.1002/anie.201913625
Angewandte Chemie International Edition
COMMUNICATION
Chem. Soc. Rev. 2013, 42, 7668–7700; h) Q. Cao, W. I. Nicholson, A.
C. Jones, D. L. Browne, Org. Biomol. Chem. 2019, 17, 1722–1726; i) Q.
Cao, J. L. Howard, E. Wheatley, D. L. Browne, Angew. Chem. Int. Ed.
2018, 57, 11339–11343; Angew. Chem. 2018, 130, 11509–11513; j) Q.
Cao, R. T. Stark, I. A. Fallis, D. L. Browne, ChemSusChem 2019, 12,
2554–2557.
that amorphous solid materials were formed after milling mixtures of 1
with one equiv of 4-ethoxyaniline or 2-phenylethanamine or (4-
methoxyphenyl)methanamine) in a mixer mill (5 min, 30 Hz), no co-
crystal formation was observed before the formation of imides (3, 4, 5).
Also, DSC analysis (30 °C-420 °C) for these reaction mixtures showed
no evidence of any co-crystal formation prior to formation of the imides.
For cocrystal controlled solid-state synthesis (C3S3) references see: a)
M. L. Cheney, G. J. McManus, J. A. Perman, Z. Wang, M. J. Zaworotko,
Crystal Growth & Design 2007, 7, 616–617; b) M. L. Cheney, M. J.
Zaworotko, S. Beaton, R. D. Singer, J. Chem. Educ. 2008, 85, 1649; c)
J. A. Perman, K. Dubois, F. Nouar, S. Zoccali, Ł. Wojtas, M. Eddaoudi,
R. W. Larsen, M. J. Zaworotko, Crystal Growth & Design 2009, 9, 5021–
5023; d) M. Colaço, J. Dubois, J. Wouters, CrystEngComm 2015, 17,
2523–2528; e) J. Dubois, M. Colaço, G. Rondelet, J. Wouters, Crystals
2016, 6, 153; (f) S. Lukin, M. Tireli, I. Lončarić, D. Barišić, P. Šket, D.
Vrsaljko, M. di Michiel, J. Plavec, K. Užarević, I. Halasz, Chem. Commun.
2018, 54, 13216–13219.
[12] For reviews see: a) J. S. L. Howard, Q. Cao, D. L. Browne, Chem. Sci.
2018, 9, 3080–3094; b) J. G. Hernández, C. Bolm, J. Org. Chem. 2017,
82, 4007–4019; c) J. L. Howard, M. C. Brand, D. L. Browne, Angew.
Chem. Int. Ed. 2018, 57, 16104–16108; Angew. Chem. 2018, 130,
16336-16340; d) J. L. Howard, Y. Sagatov, L. Repusseau, C. Schotten,
D. L. Browne, Green Chem. 2017, 41, 413.
[13] a) A. Stolle, R. Schmidt, K. Jacob, Faraday Discuss. 2014, 170, 267–
286; b) R. G. Blair, K. Chagoya, S. Biltek, S. Jackson, A. Sinclair, A.
Taraboletti, D. T. Restrepo, Faraday Discuss. 2014, 170, 223–233; c) D.
W. Peters, R. G. Blair, Faraday Discuss. 2014, 170, 83–91; d) X. Ma, G.
K. Lim, K. D. M. Harris, D. C. Apperley, P. N. Horton, M. B. Hursthouse,
S. L. James, Crystal Growth & Design 2012, 12, 5869–5872.
[30] a) M. Mazhar, M. Abdouss, K. Gharanjig, R. Teimuri-Mofrad, Prog Org
Coat 2016, 101, 297–304; b) K.-Y. Tomizaki, P. Thamyongkit, R. S.
Loewe, J. S. Lindsey, Tetrahedron 2003, 59, 1191–1207; c) S. P. Black,
D. M. Wood, F. B. Schwarz, T. K. Ronson, J. J. Holstein, A. R.
Stefankiewicz, C. A. Schalley, J. K. M. Sanders, J. R. Nitschke, Chem.
Sci. 2016, 7, 2614–2620; d) S. P. Black, A. R. Stefankiewicz, M. M. J.
Smulders, D. Sattler, C. A. Schalley, J. R. Nitschke, J. K. M. Sanders,
Angew. Chem. Int. Ed. 2013, 52, 5749–5752; Angew. Chem. 2013, 125,
5861-5864; e) J. Choi, C. Sakong, J.-H. Choi, C. Yoon, J. P. Kim, Dyes
Pigm 2011, 90, 82–88. f) H. Wang, L. Yang, K. Li, Y. Wei, X. Zhu, CN
104402930B, 2014.
[14] a) D. Douroumis, S. A. Ross, A. Nokhodchi, Adv. Drug. Deliv. Rev. 2017,
117, 178–195; b) R. B. Chavan, R. Thipparaboina, B. Yadav, N. R.
Shastri, Drug Deliv. and Transl. Res. 2018, 1–14; c) R. S. Dhumal, A. L.
Kelly, P. York, P. D. Coates, A. Paradkar, Pharm. Res. 2010, 27, 2725–
2733; d)
M. A. Repka, S. Bandari, V. R. Kallakunta, A. Q. Vo, H.
McFall, M. B. Pimparade, A. M. Bhagurkar, Int. J. Pharm. 2018, 535, 68–
85; e) D. Braga, L. Maini, F. Grepioni, Chem. Soc. Rev. 2013, 42, 7638;
f) T. Stolar, S. Lukin, M. Tireli, I. Sović, B. Karadeniz, I. Kereković, G.
Matijašić, M. Gretić, Z. Katančić, I. Dejanović, et al., ACS Sustainable
Chem. Eng. 2019, 7, 7102–7110.
[15] a) C. Tzoganakis, Adv. Polym. Technol. 1989, 9, 321–330; b) J. Jordan,
K. I. Jacob, R. Tannenbaum, M. A. Sharaf, I. Jasiuk, Mater Sci. Eng. A.
2005, 393, 1–11.
[31] a) C. Rosso, J. D. Williams, G. Filippini, M. Prato, C. O. Kappe, Org. Lett.
2019, 21, 5341–5345; b) L. Li, Y.-J. Hong, D.-Y. Chen, M.-J. Lin, Chem.
Eur. J. 2017, 23, 16612–16620; c) R. Regar, R. Mishra, P. K. Mondal, J.
Sankar, J. Org. Chem. 2018, 83, 9547–9552; d) L. Li, Y.-J. Hong, D.-Y.
Chen, M.-J. Lin, Chem. Eur. J. 2017, 23, 16612–16620.
[16] a)
N. Castro, V. Durrieu, C. Raynaud, A. Rouilly, L. Rigal, C. Quellet,
Polym. Rev. 2016, 56, 137–186; b) V. Offiah, V. Kontogiorgos, K. O.
Falade, Crit. Rev. Food. Sci. Nutr. 2018, 1–20.
[32] The price of Pigment Black 31 and 32 are viewed on 14 October 2019:
[17] D. Crawford, J. Casaban, R. Haydon, N. Giri, T. McNally, S. L. James,
Chem. Sci. 2015, 6, 1645–1649.
[18] D. E. Crawford, L. A. Wright, S. L. James, A. P. Abbott, Chem. Commun.
2016, 52, 4215–4218.
®ion=GB&cm_sp=Insite-_-prodRecCold_xviews-_-prodRecCold10-1
[33] The price of PTCDA are viewed on 14 October 2019:
[19] D. E. Crawford, S. L. James, T. McNally, ACS Sustainable Chem. Eng.
2017, 6, 193–201.
[20] D. E. Crawford, C. K. G. Miskimmin, A. B. Albadarin, G. Walker, S. L.
James, Green Chem. 2017, 19, 1507–1518.
[34] The price of 2-phenylethanamine are viewed on 14 October 2019:
®ion=GB
[21] K. J. Ardila-Fierro, D. E. Crawford, A. Körner, S. L. James, C. Bolm, J.
G. Hernández, Green Chem. 2018, 20, 1262–1269.
[22] Q. Cao, J. L. Howard, D. E. Crawford, S. L. James, D. L. Browne, Green
Chem. 2018, 20, 4443–4447.
[35] The price of 4-methoxybenzylamine are viewed on 14 October 2019:
[23] D. E. Crawford, C. K. Miskimmin, J. Cahir, S. L. James, Chem. Commun.
2017, 53, 13067–13070.
[36] a) M. Mazhar, M. Abdouss, K. Gharanjig, R. Teimuri-Mofrad, Prog. Org.
Coatings, 2016, 101, 297–304; b) J. Xie, W. Liu, Y. Liu, S. Jian, H. Wang,
L. Deng, CN 105694531, 2016; c) Y. Shen, K. Yan, Z. Zhang, Z. Zhang,
X. Bai, W. Zhang, CN 1654546, 2005,; d) J. Zhou, W. Zhang, X.-F. Jiang,
C. Wang, X. Zhou, B. Xu, L. Liu, Z. Xie, Y. Ma, J. Phys. Chem. Lett. 2018,
9, 596–600; e) J. LÖBEL, WO 2009074504, 2009; f) H. Spahni, J.
Mizuguchi, B. Schmidhalter, A. Wolleb, J. Budry, G.Giller, WO9849164,
1998,; g) J. M. Duff, Ah-Mee. Hor, C.G. Allen, US 5853933, 1998.
[24] F. Gomllón-Bel, Chem. Int., 2019, 41, 12-17.
[25] G. Kaupp, J. Schmeyers, J. Boy, Tetrahedron. 2000, 56, 6899–6911.
[26] G. Beyer, C. Hopmann, Reactive Extrusion: Principles and Applications,
Wiley-VCH: Weinheim, 2017, pp. 22-27.
[27] A. R. West, Solid State Chemistry and its Application, Wiley-VCH:
Weinheim, 2014, pp. 183-195.
[37] F .M. Eissa, N. S. Mohamed, J. Chem. Eng. Process. Technol. 2018, 9,
[28] I. P. Parkin, Encyclopedia of Materials: Science and Techonology,
Elsevier Science Ltd, New York, 2001, pp. 8675-8679.
389
[38] L.P. Jameson, S. V. Dzyuba, Beilstein J. Org. Chem. 2018, 9, 786-790.
[29] There are two relevant questions around the mechanism of the reaction,
specifically whether the reaction occurs in the melt or solid phase, and
secondly whether the reactants form co-crystal prior to the bond
formation. First, whilst we do not observe any bulk melting in these
reactions (as can be expected since the reactant melting points are high
(1,8-naphthalic anhydride, 267oC; PTCDA 350oC). We currently do not
draw any conclusions about solid versus liquid states existing at the
actual reaction zones. Also, although some of the amines used are
liquids, and it is unlikely that the anhydrides will fully dissolve in them, we
cannot rule out that some dissolution occurs. Secondly, co-crystals,
formed from anhydrides and anilines, have been reported under neat or
liquid assisted grinding conditions, which facilitates subsequent imide
formation upon heating. However, in our work PXRD analysis showed
This article is protected by copyright. All rights reserved.