effect to afford specific metallacycles. More significantly, anion-π interactions
showed ability to drive charge-neutral building blocks and anions into various
self-assemblies. With rational designed organic building blocks, the strength and
directionality of anion-π interactions could be enhanced; this and along with the
intriguing reversibility and easy regulation endow it a promising driving force in
rational designed and functional self-assembly.
References
1. Schneider H-J, Werner F, Blatter T (1993) Attractive interactions between negative charges and
polarizable aryl parts of host-guest systems. J Phys Org Chem 6:590–594
2. Mascal M, Armstrong A, Bartberger MD (2002) Anion-aromatic bonding: a case for anion
recognition by π-acidic rings. J Am Chem Soc 124:6274–6276
3. Quiñonero D, Garau C, Rotger C, Frontera A, Ballester P, Costa A, Deyà PM (2002) Anion-π
interactions: do they exist? Angew Chem Int Ed 41:3389–3392
4. Alkorta I, Rozas I, Elguero J (2002) Interaction of anions with perfluoro aromatic compounds.
J Am Chem Soc 124:8593–8598
5. Wang D-X, Wang M-X (2011) Anion recognition by charge neutral electron-deficient arene
receptors. Chimia 65:939–943
6. Hay BP, Bryantsev VS (2008) Anion-arene adducts: C-H hydrogen bonding, anion-π interaction, and carbon bonding motifs. Chem Commun 2008:2417–2428
7. Berryman OB, Johnson DW (2009) Experimental evidence for interactions between anions and
electron-deficient aromatic rings. Chem Commun 3143–3153
8. Ballester PB (2013) Experimental quantification of anion-π interactions in solution using
neutral host-guest model systems. Acc Chem Res 46:874–884
9. Giese M, Albrecht M, Rissanen K (2015) Anion-π interactions with fluoroarenes. Chem Rev
115:8867–8895
10. Zhao Y, Cotelle Y, Liu L, López-Andarias J, Bornhof A-B, Akamatsu M, Sakai N, Matile S
(2018) The emergence of anion-π catalysis. Acc Chem Res 51:2255–2263
11. Saha S (2018) Anion-induced electron transfer. Acc Chem Res 51:2225–2236
12. Chifotides HT, Schottel BL, Dunbar KR (2010) The π-accepting arene HAT(CN) 6 as a halide
receptor through charge transfer: multisite anion interactions and self-assembly in solution and
the solid state. Angew Chem Int Ed 49:7202–7207
13. Aragay G, Frontera A, Lloveras V, Vidal-Gancedo J, Ballester P (2013) Different nature of the
interactions between anions and HAT(CN) 6 : from reversible anion-π complexes to irreversible
electron-transfer processes (HAT(CN) 6 = 1,4,5,8,9,12-hexaazatriphenylene). J Am Chem Soc
135:2620–2627
14. Dougherty DA (2013) The cation-π interaction. Acc Chem Res 46:885–893
15. Alkorta I, Rozas I, Elguero J (1997) An attractive interaction between the π-cloud of C 6 F 6 and
electron-donor atoms. J Org Chem 62:4687–4691
16. Gallivan JP, Dougherty DA (1999) Can lone pairs bind to a π system? The water. . .hexafluorobenzene interaction. Org Lett 1:103–105
17. Danten Y, Tassaing T, Besnard M (1999) On the nature of the water-hexafluorobenzene
interaction. J Phys Chem A 103:3530–3534
18. Kim D, Tarakeshwar P, Kim KS (2004) Theoretical investigations of anion-π interactions: the
role of anions and the nature of π systems. J Phys Chem A 108:1250–1258
19. Berryman OB, Bryantsev VS, Stay DP, Johnson DW, Hay BP (2007) Structural criteria for the
design of anion receptors: the interaction of halides with electron-deficient arenes. J Am Chem
Soc 129:48–58
20. Xi J, Xu X (2016) Understanding the anion-π interactions with tetraoxacalix[2]arene[2]triazine.
Phys Chem Chem Phys 18:6913–6924
10 Application of Anion-π Interaction on Supramolecular Self-Assembly
273
showed ability to drive charge-neutral building blocks and anions into various
self-assemblies. With rational designed organic building blocks, the strength and
directionality of anion-π interactions could be enhanced; this and along with the
intriguing reversibility and easy regulation endow it a promising driving force in
rational designed and functional self-assembly.
References
1. Schneider H-J, Werner F, Blatter T (1993) Attractive interactions between negative charges and
polarizable aryl parts of host-guest systems. J Phys Org Chem 6:590–594
2. Mascal M, Armstrong A, Bartberger MD (2002) Anion-aromatic bonding: a case for anion
recognition by π-acidic rings. J Am Chem Soc 124:6274–6276
3. Quiñonero D, Garau C, Rotger C, Frontera A, Ballester P, Costa A, Deyà PM (2002) Anion-π
interactions: do they exist? Angew Chem Int Ed 41:3389–3392
4. Alkorta I, Rozas I, Elguero J (2002) Interaction of anions with perfluoro aromatic compounds.
J Am Chem Soc 124:8593–8598
5. Wang D-X, Wang M-X (2011) Anion recognition by charge neutral electron-deficient arene
receptors. Chimia 65:939–943
6. Hay BP, Bryantsev VS (2008) Anion-arene adducts: C-H hydrogen bonding, anion-π interaction, and carbon bonding motifs. Chem Commun 2008:2417–2428
7. Berryman OB, Johnson DW (2009) Experimental evidence for interactions between anions and
electron-deficient aromatic rings. Chem Commun 3143–3153
8. Ballester PB (2013) Experimental quantification of anion-π interactions in solution using
neutral host-guest model systems. Acc Chem Res 46:874–884
9. Giese M, Albrecht M, Rissanen K (2015) Anion-π interactions with fluoroarenes. Chem Rev
115:8867–8895
10. Zhao Y, Cotelle Y, Liu L, López-Andarias J, Bornhof A-B, Akamatsu M, Sakai N, Matile S
(2018) The emergence of anion-π catalysis. Acc Chem Res 51:2255–2263
11. Saha S (2018) Anion-induced electron transfer. Acc Chem Res 51:2225–2236
12. Chifotides HT, Schottel BL, Dunbar KR (2010) The π-accepting arene HAT(CN) 6 as a halide
receptor through charge transfer: multisite anion interactions and self-assembly in solution and
the solid state. Angew Chem Int Ed 49:7202–7207
13. Aragay G, Frontera A, Lloveras V, Vidal-Gancedo J, Ballester P (2013) Different nature of the
interactions between anions and HAT(CN) 6 : from reversible anion-π complexes to irreversible
electron-transfer processes (HAT(CN) 6 = 1,4,5,8,9,12-hexaazatriphenylene). J Am Chem Soc
135:2620–2627
14. Dougherty DA (2013) The cation-π interaction. Acc Chem Res 46:885–893
15. Alkorta I, Rozas I, Elguero J (1997) An attractive interaction between the π-cloud of C 6 F 6 and
electron-donor atoms. J Org Chem 62:4687–4691
16. Gallivan JP, Dougherty DA (1999) Can lone pairs bind to a π system? The water. . .hexafluorobenzene interaction. Org Lett 1:103–105
17. Danten Y, Tassaing T, Besnard M (1999) On the nature of the water-hexafluorobenzene
interaction. J Phys Chem A 103:3530–3534
18. Kim D, Tarakeshwar P, Kim KS (2004) Theoretical investigations of anion-π interactions: the
role of anions and the nature of π systems. J Phys Chem A 108:1250–1258
19. Berryman OB, Bryantsev VS, Stay DP, Johnson DW, Hay BP (2007) Structural criteria for the
design of anion receptors: the interaction of halides with electron-deficient arenes. J Am Chem
Soc 129:48–58
20. Xi J, Xu X (2016) Understanding the anion-π interactions with tetraoxacalix[2]arene[2]triazine.
Phys Chem Chem Phys 18:6913–6924
10 Application of Anion-π Interaction on Supramolecular Self-Assembly
273