Resorcinarenes - Gears of Supramolecular Chemistry

Resourceful Design and Custom Synthesis for Successful Outsourcing
17 January 2023
Alexander Shivanyuk
DSc, Professor
Chief Scientific Officer

Resorcinarenes [1] are known to be versatile macrocyclic platforms for many covalent and supramolecular assemblies serving a variety of applications, e.g., ion-channel mimics [2], catalysis [3], and drug delivery [4]. Parent resorcin[4]arenes 1 (Fig. 1) form capsular complexes in solution and self-assemble at interfaces. Upon proper functionalization, resorcin[4]arenes turn into their rigidified derivatives called cavitands, such as 4 [5] and closed-shell compounds termed carcerands [6]. These compounds are capable of reversible or irreversible binding of different molecular guests.

It should be pointed out that the isolation of highly unstable cyclobuta-1,3-diene at room temperature inside a carcerand [7] is one of the most impressive examples of resorcin[4]arene applications. Regioselective acylation of resorcin[4]arenes gives tetrasubstituted compounds 2 [8]. Tetraphosphates 2a and tetraaroylates 2b were shown to form capsular dimeric complexes with cationic guests [9]. Tetrasulfonates 2c (in which Ar = 2-naphthyl) assemble into UV-polymerizable monolayers at the air/water interface [10], while distally bridged tetrasulfonates were suggested as templates for asymmetric catalysis [11]. Aminomethylated resorcin[4]arene derivatives 3 form kinetically stable complexes with halide anions [12] and small molecules, e.g., acetonitrile [13].

Life Chemicals offers highly effective custom synthesis of functionalized resorcin[4]- and [6]arene derivatives, such as the ones shown in Fig. 1. For more structural examples, see the relevant references.

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Figure 1. Representative structures of the resorcinarenes, available upon request from Life Chemicals.


  1. (a) Sliwa, W.; Kozlowski, C. Calixarenes and resorcinarenes. 2009, Wiley VCH, Weinheim. (b) Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663–2704.
  2. Wright, A. J.; Matthews, S. E.; Fischer, W. B.; Beer, P. D. Chem. Eur. J. 2001, 7, 3474–3481.
  3. Zhang, Q.; Catti, L.; Tiefenbacher, K. Acc. Chem. Res. 2018, 51, 2107–2114.
  4. Shumatbaeva, A. M.; Morozova, J. E.; Syakaev, V. V. et al. Colloids Surf. A Physicochem. Eng. 2020, 589, 124453.
  5. Körner, S. K.; Tucci, F. C.; Rudkevich, D. M.; Heinz, T.; Rebek, J. Jr. Chem. Eur. J. 2000, 6, 187–195.
  6. Cram, D. J.; Cram, J. M. Container Molecules and Their Guests 1997, The Royal Society of Chemistry, London.
  7.  Cram, D. J.; Tanner, M. E.; Thomas, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 1024.
  8. (a) Kalchenko, V. I.; Rudkevich, D. M.; Shivanyuk, A. N.; Pirozhenko, V. V.; Tsymbal, I. F.; Markovsky, L. N. Zh. Obshch. Khim. 1994, 64, 731–742; Russ. J. Gen. Chem. 1994, 64, 663–672. (b) Lukin, O.; Pirozhenko, V. V.; Shivanyuk, A. N. Tetrahedron Lett. 1995, 36, 7725–7728. (c) Shivanyuk, A.; Paulus, E. F.; Böhmer, V.; Vogt, W. J. Org. Chem. 1998, 63, 6448–6449.
  9. (a) Shivanyuk, A.; Paulus, E. F.; Böhmer, V. Angew. Chem. Int. Ed. 1999, 38, 2906–2909. (b) Shivanyuk, A. Tetrahedron 2005, 61, 349–352
  10.  Semenok, D.; Kletskov, A.; Burilov, V.; Luchkin, S.; Potkin, V.; Lukin, O. Mater. Today Commun. 2020, 25, 101334.
  11. Arnott, G.; Hunter, R. Tetrahedron 2006, 62, 992–1000.
  12. Shivanyuk, A.; Spaniol, T. P.; Rissanen, K.; Kolehmainen, E.; Böhmer, V. Angew. Chem., Int. Ed. 2000, 39, 3497–3500.
  13.  Falábu, D.; Shivanyuk, A.; Nissinen, M.; Rissanen, K. Org. Lett. 2002, 4, 3019–3022.
17 January 2023, 15:49 Alexander Shivanyuk Custom synthesis

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