Abstract
In order to systematically explore the general rule of the host-guest chemistry for pillararenes, this work investigates the weak interactions between pillar[4]arene and some typical guests (anions, cations, and dumbbell-shaped molecules) by using density functional theory (DFT) calculations at the ωB97XD/6-311G(d,p) level. The strong molecular recognition ability of pillar[4]arene has been discussed based on the geometry structure, electronic structure, and thermodynamic properties of the host-guest complexes. The results show that the equivalent lower and upper rims of the pillar[4]arene can be combined with both anion and cation, and its cavity can accommodate the alkyl part of the dumbbell-shaped molecule. The main host-guest interactions between pillar[4]arene and guests are hydrogen bond, cation-π, anion-π, and hydrophobic interaction by visualization of weak interactions using the Multiwfn program. Pillar[4]arene will form a more stable host-guest complex with the guest, which possesses conjugate structure and weak steric repulsion. This work intends to provide a theoretical basis for enriching the host-guest chemistry, understanding the supramolecular morphology, and expanding the applications of the pillararenes.
Similar content being viewed by others
References
Ogoshi T, Kanai S, Fujinami S, Yamagishi TA, Nakamoto Y (2008) J Am Chem Soc 130:5022
Guo F, Sun Y, Xi BH, Diao GW (2018) Supramol Chem 30:81
Wang P, Li Z, Ji X (2014) Chem Commun 50:13114
Fan JZ, Deng HM, Li J, Jia XS, Li CJ (2013) Chem Commun 49:6343
Chen LX, Wang Y, Yuan XY, Ren Y, Liu N, Yuan LH, Feng W (2018) Sep Purif Technol 192:152
Ogoshi T, Saito K, Sueto R, Kojima R, Hamada Y, Akine S, Moeljadi AMP, Hirao H, Kakuta T, Yamagishi T (2018) Angew Chem 57:1592
Xue M, Yang Y, Chi XD, Zhang ZB, Huang FH (2012) Acc Chem Res 45:1294
Strutt NL, Fairen Jimenez D, Iehl J, Lalonde MB, Snurr RQ, Farha OK, Hupp JT, Stoddart JF (2012) J Am Chem Soc 134:17436
Xia DY (2017) Host-guest recognition based on pillar[6]arenes and their applications. Zhejiang University, Hangzhou
Li C, Ma JW, Zhao L, Zhang YY, Yu YH, Shu XY, Li J, Jia XS (2013) Chem Commun 49:1924
Xia B, Xue M (2014) Chem Commun 50:1021
Venkataramanan NS, Suvitha A, Thamotharan AVS (2017) Mol Liq 241:782
Frisch MJ, Trucks GW, Schlegel HB et al (2010) Gaussian 09, revision B. 01. Gaussian Inc., Wallingford
Chai JD, Gordon MH (2008) J Chem Phys 128:084106
Reed AE, Weinhold F, Curtiss LA, Pochatko DJ (1986) Chem Phys 84:5687
Reed AE, Curtiss LA, Weinhold F (1988) Chem Rev 88:899
Lu T, Chen FW (2012) J Comput Chem 33:58
Humphrey W, Dalke A, Schulten K (1996) J Mol Graph 14:33
Johnson ER, Keinan S, Mori-Sanchez P, Contreras-Garcia J, Cohen AJ, Yang W (2010) J Am Chem Soc 132:6498
Saleh G, Gatti C, Lo Presti L, Contreras-Garcia J (2012) Chem Eur J 18:15523
Pan S, Mondal S, Chattaraj PK (2013) New J Chem 37:2492
Lo R, Ganguly B (2015) J Mol Graph Model 55:123
Kozmon S, Matuška R, Spiwok V, Koča J (2011). Phys Chem Chem Phys 13:14215
Zhao C, Li P, Mark D, Smith PJP, Ken DS (2014) Org Lett 16:3520
Acknowledgments
This work was supported by Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD); Top-notch Academic Programs Project of Jiangsu Higher Education Institutions (TAPP, PPZY2015B112); 111 Project, B12015; Postgraduate Research & Practice Innovation Program of Jiangsu Province (XKYCX17_037), and Science and Technology Innovation Foundation for Students of Yangzhou University (No. 313).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no ethical conflicts and competing financial interests.
Rights and permissions
About this article
Cite this article
Shen, C., Gong, Z., Gao, L. et al. Theoretical study on host-guest interaction between pillar[4]arene and molecules or ions. J Mol Model 24, 199 (2018). https://doi.org/10.1007/s00894-018-3736-2
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s00894-018-3736-2