Resorcinarene Derivatives

Resorcinarenes [1] are versatile macrocyclic platforms widely recognized for their role in various covalent and supramolecular assemblies with applications in ion-channel mimics [2], catalysis [3], and drug delivery [4].

Our chemists offer highly efficient custom synthesis of functionalized resorcin[4]—and [6]arene derivatives, such as the ones shown in Fig. 1. These functionalized resorcinarenes offer a broad range of possibilities for innovative applications in chemistry, drug discovery, and materials sciences.

Please, contact us at orders@lifechemicals.com for any additional information and price quotations.

You can also be interested in our related products:

• Custom Synthesis Services
• Building Blocks
• Peptidomimetic Compound Library

For related topics, please refer to our MedChem blog on Building Blocks and Custom synthesis.

Applications of resorcinarene derivatives

The parent resorcin[4]arenes 1 (Fig. 1) are known to form capsular complexes in solution and self-assemble at interfaces. Upon appropriate functionalization, these resorcin[4]arenes can be transformed into more rigid derivatives called cavitands, such as example 4 [5], and closed-shell compounds known as carcerands [6], which are capable of reversible or irreversible binding of various molecular guests.

One of the most remarkable applications of resorcin[4]arenes is the isolation of highly unstable cyclobuta-1,3-diene at room temperature within a carcerand [7]. Regioselective acylation of resorcin[4]arenes produces tetrasubstituted compounds 2 [8]. These include tetraphosphates 2a and tetraaroylates 2b, known to form capsular dimeric complexes with cationic guests [9]. Additionally, tetrasulfonates 2c (where Ar = 2-naphthyl) can assemble into UV-polymerizable monolayers at the air/water interface [10], and distally bridged tetrasulfonates have been proposed as templates for asymmetric catalysis [11]. Moreover, aminomethylated resorcin[4]arene derivatives 3 are capable of forming kinetically stable complexes with halide anions [12] and small molecules such as acetonitrile [13].

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

Reference:

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.