Highly Fluorinated Trianglimine Macrocycles: A Supramolecular Organic Framework

Tom Kunde; Tobias Pausch; Guido J. Reiss; Bernd M. Schmidt

doi:10.1055/a-1470-6050

Synlett, Table of Contents

Synlett 2022; 33(02): 161-165
DOI: 10.1055/a-1470-6050

letter

EuCheMS Organic Division Young Investigator Workshop

Highly Fluorinated Trianglimine Macrocycles: A Supramolecular Organic Framework

Tom Kunde‡

^aInstitut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany

,

Tobias Pausch‡

^aInstitut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany

,

Guido J. Reiss

^bInstitut für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany

,

Bernd M. Schmidt ∗

^aInstitut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany

› Author Affiliations

Abstract

All articles of this category

Abstract

A novel highly fluorinated dialdehyde was prepared by a two-stage synthesis. This reactive building block for dynamic imine chemistry was used in a condensation reaction to generate the first extensively fluorinated trianglimine. An analysis of the material properties and, especially, the crystal structure of the [3+3] macrocycle revealed a supramolecular organic framework with tubular porous channels. The use of fluorinated ligands to generate hydrophobic electron-deficient channel-like pores is an important addition to the ever-expanding field of supramolecular networks and to trianglimine chemistry in general.

Key words

supramolecular organic frameworks - trianglimines - porous materials - fluorinated ligands - crystal structure

Full Text

References

References and Notes

1a Rosi NL, Eckert J, Eddaoudi M, Vodak DT, Kim J, O’Keeffe M, Yaghi OM. Science 2003; 300: 1127
1b Chen T.-H, Popov I, Chuang Y.-C, Chen Y.-S, Miljanić O. Š. Chem. Commun. 2015; 51: 6340
1c Küsgens P, Zgaverdea A, Fritz H, Siegle S, Kaskel S. J. Am. Ceram. Soc. 2010; 93: 2476

For reviews, see:

1d Yuan S, Feng L, Wang K, Pang J, Bosch M, Lollar C, Sun Y, Qin J, Yang X, Zhang P, Wang Q, Zou L, Zhang Y, Zhang L, Fang Y, Li J, Zhou H.-C. Adv. Mater (Weinheim, Ger.) 2018; 30: 1704303
1e Furukawa H, Cordova KE, O’Keeffe M, Yaghi OM. Science 2013; 341: 1230444
1f James SL. Chem. Soc. Rev. 2003; 32: 276

2a Vyas VS, Haase F, Stegbauer L, Savasci G, Podjaski F, Ochsenfeld C, Lotsch BV. Nat. Commun. 2015; 6: 8508
2b Yang H, Du Y, Wan S, Trahan GD, Jin Y, Zhang W. Chem. Sci. 2015; 6: 4049
2c Chen X, Addicoat M, Irle S, Nagai A, Jiang D. J. Am. Chem. Soc. 2013; 135: 546
2d Doonan CJ, Tranchemontagne DJ, Glover TG, Hunt JR, Yaghi OM. Nat. Chem. 2010; 2: 235
2e Uribe-Romo FJ, Hunt JR, Furukawa H, Klöck C, O’Keeffe M, Yaghi OM. J. Am. Chem. Soc. 2009; 131: 4570

For reviews, see:

2f Beuerle F, Gole B. Angew. Chem. Int. Ed. 2018; 57: 4850
2g Ding S.-Y, Wang W. Chem. Soc. Rev. 2013; 42: 548

3a Yang W, Greenaway A, Lin X, Matsuda R, Blake AJ, Wilson C, Lewis W, Hubberstey P, Kitagawa S, Champness NR, Schröder M. J. Am. Chem. Soc. 2010; 132: 14457
3b Tan L, Li H, Tao Y, Zhang SX, Wang B, Yang Y. Adv. Mater (Weinheim, Ger.) 2014; 26: 7027
3c Lü J, Perez-Krap C, Suyetin M, Alsmail NH, Yan Y, Yang S, Lewis W, Bichoutskaia E, Tang CC, Blake AJ, Cao R, Schröder M. J. Am. Chem. Soc. 2014; 136: 12828
3d Pfeffermann M, Dong R, Graf R, Zajaczkowski W, Gorelik T, Pisula W, Narita A, Müllen K, Feng X. J. Am. Chem. Soc. 2015; 137: 14525
3e Chen T.-H, Kaveevivitchai W, Jacobson AJ, Miljanić O. Š. Chem. Commun. 2015; 51: 14096
3f Huang Y.-G, Shiota Y, Wu M.-Y, Su S.-Q, Yao Z.-S, Kang S, Kanegawa S, Li G.-L, Wu S.-Q, Kamachi T, Yoshizawa K, Ariga K, Hong M.-C, Sato O. Nat. Commun. 2016; 7: 11564
3g Zhang G, Li B, Zhou Y, Chen X, Li B, Lu Z.-Y, Wu L. Nat. Commun. 2020; 11: 425

4a Yang H, Du Y, Wan S, Trahan GD, Jin Y, Zhang W. Chem. Sci. 2015; 6: 4049
4b Hisaki I, Nakagawa S, Tohnai N, Miyata M. Angew. Chem. Int. Ed. 2015; 54: 3008
4c Qi Z, Schalley CA. Acc. Chem. Res. 2014; 47: 2222
4d Reuter R, Wegner HA. Chem. Commun. 2013; 49: 146
4e Huang Z, Kang S.-K, Banno M, Yamaguchi T, Lee D, Seok C, Yashima E, Lee M. Science 2012; 337: 1521
4f Venkataraman D, Lee S, Zhang J, Moore JS. Nature 1994; 371: 591

5a Kuhnert N, Straßnig C, Lopez-Periago AM. Tetrahedron: Asymmetry 2002; 13: 123
5b Kuhnert N, Lopez-Periago AM. Tetrahedron Lett. 2002; 43: 3329
5c Kuhnert N, Burzlaff N, Patel C, Lopez-Periago A. Org. Biomol. Chem. 2005; 3: 1911
5d Nour HF, Matei MF, Bassil BS, Kortz U, Kuhnert N. Org. Biomol. Chem. 2011; 9: 3258
5e Wang Z, Nour HF, Roch LM, Guo M, Li W, Baldridge KK, Sue AC.-H, Olson MA. J. Org. Chem. 2017; 82: 2472
5f Szymkowiak J, Warżajtis B, Rychlewska U, Kwit M. CrystEngComm 2018; 20: 5200
5g Dey A, Chand S, Alimi LO, Ghosh M, Cavallo L, Khashab NM. J. Am. Chem. Soc. 2020; 142: 15823

6a Gawroński J, Gawrońska K, Grajewski J, Kwit M, Plutecka A, Rychlewska U. Chem. Eur. J. 2006; 12: 1807
6b Kuhnert N, Göbel D, Thiele C, Renault B, Tang B. Tetrahedron Lett. 2006; 47: 6915
6c Nour HF, Matei MF, Bassil BS, Kortz U, Kuhnert N. Org. Biomol. Chem. 2011; 9: 3258
6d Janiak A, Bardziński M, Gawroński J, Rychlewska U. Cryst. Growth Des. 2016; 16: 2779
6e Chaix A, Mouchaham G, Shkurenko A, Hoang P, Moosa B, Bhatt PM, Adil K, Salama KN, Eddaoudi M, Khashab NM. J. Am. Chem. Soc. 2018; 140: 14571
6f Huang T, Moosa BA, Hoang P, Liu J, Chisca S, Zhang G, AlYami M, Khashab NM, Nunes SP. Nat. Commun. 2020; 11: 5882
6g Dey A, Chand S, Maity B, Bhatt PM, Ghosh M, Cavallo L, Eddaoudi M, Khashab NM. J. Am. Chem. Soc. 2021; 143: 4090

7a Yang Z, Wang S, Zhang Z, Guo W, Jie K, Hashim MI, Miljanić O. Š, Jiang D.-e, Popovs I, Dai S. J. Mater. Chem. A 2019; 7: 17277
7b Cadiau A, Belmabkhout Y, Adil K, Bhatt PM, Pillai RS, Shkurenko A, Martineau-Corcos C, Maurin G, Eddaoudi M. Science 2017; 356: 731
7c Chen T.-H, Popov I, Kaveevivitchai W, Chuang Y.-C, Chen Y.-S, Jacobson AJ, Miljanić O. Š. Angew. Chem. Int. Ed. 2015; 54: 13902
7d Chen T.-H, Popov I, Zenasni O, Daugulis O, Miljanić O. Š. Chem. Commun. 2013; 49: 6846
7e Babudri F, Farinola GM, Naso F, Ragni R. Chem. Commun. 2007; 1003

For an excellent review, see:

7f Zhang Z, Miljanić O. Š. Org. Mater. 2019; 1: 19

8 Kaneko T. JP 2006273766, 2006
9 Kolomeitsev AA, Seifert FU, Röschenthaler G.-V. J. Fluorine Chem. 1995; 71: 47
10 Hérault D, Nguyen DH, Nuel D, Buono G. Chem. Soc. Rev. 2015; 44: 2508
11 Supramolecular Organic Framework RRF24 A solution of DACH (91.4 mg, 800 μmol, 1.0 equiv) in MeCN (15 mL) was added dropwise to a stirred solution of dialdehyde 2 (283 mg, 800 μmol, 1.0 equiv) in MeCN (10 mL) over 1 h. The resulting solution was stirred overnight at r.t., and the precipitate that formed was collected by filtration and washed with MeCN (2 × 5 mL) to give a colorless powder; yield: 195 mg (150 μmol, 56%); mp 306.7 °C. FTIR (ATR): 2933.7 (w), 2862.4 (w), 1643.4 (w), 1469.8 (s), 1384.9 (w)1278.8 (m), 1263.4 (w), 1089.8 (w), 1033.9 (w), 987.6 (m), 927.8 (m), 862.2 (w), 723.3 (s) cm^–1. ¹H NMR (300 MHz, CDCl₃): δ = 8.40 (s, 2 H, –CH_AN), 3.84–3.22 (m, 2 H, CH–N=), 2.12–1.72 (m, 6 H, –C(H_B)₂– and C–H_C), 1.75–1.34 (m, 2 H, C–H_C). ¹³C{¹H} NMR (126 MHz, CDCl₃): δ = 149.7 (Ar–CH_AO), 145.6 (dd, J = 257.3, 11.8 Hz, C_Ar–F_A), 143.7 (dd, J = 254.5, 15.5 Hz, C_Ar–F_B), 117.9 (t, J = 12.7 Hz, C_Ar–CH_AO), 108.1 (t, J = 16.2 Hz, Ar–C_Ar), 76.0 (–C–N=), 32.4 (–C–H_B), 24.3 (–C–H_B). ¹⁹F NMR (282 MHz, CDCl₃): δ –137.77 (dd, J = 16.8, 9.6 Hz, 4 F, Ar–F_A), –142.38 to –143.31 (m, 4 F, Ar–F_B). HRMS (ESI): m/z [M + H]⁺ Calcd for C₆₀H₃₇F₂₄N₆ = 1297.2691; found: 1297.2688.

12a Dittrich B, Bergmann J, Roloff P, Reiss GJ. Crystals 2018; 8: 213
12b Reiß GJ. Acta Crystallogr., Sect. E 2002; 58: m47

13a Kunde T, Nieland E, Schröder HV, Schalley CA, Schmidt BM. Chem. Commun. 2020; 56: 4761
13b Schmidt BM, Meyer AK, Lentz D. CrystEngComm 2017; 19: 1328

Supplementary Material

Supporting Information