by employing the host-guest properties of pillararenes for their facile modification
and intrinsically intriguing inclusion properties. Moreover, due to the dynamic
nature of the noncovalent interaction between pillar[n]arene and corresponding
guest molecules, these assemblies exhibited excellent responsiveness to external
stimuli, such as pH, concentration, solvent polarity, temperature, photochemistry,
and competitive components. Therefore, they might have potential application
into the chemical sensors, stimuli-responsive materials, and optical materials.
However, compared to crown ethers, cyclodextrins, calixarenes, and
cucurbiturils, it is still an immature project to build pillararene-based supramolecular
polymers. There are a lot of challenges and opportunities in this emerging research
field. Firstly, although various pillar[n]arene-based supramolecular polymer was
successfully constructed, little efforts had been engaged in the research their properties and applications, especially in the energy and environment fields. Secondly, to
date most researches were conducted in the organic solvent and mainly focused on
the pillar[5]arene and pillar[6]arene, which would limit their potential application in
the biological fields as well as the real life. Finally, how to combine the lab research
with the industrial production was still the barrier to overcome.
References
1. (a) Cao D, Kou Y, Liang J, Chen Z, Wang L, Meier H (2009) A facile and efficient preparation
of pillararenes and a pillarquinone. Angew Chem Int Ed 48:9721–9723; (b) Ogoshi T, Kanai S,
Fujinami S, Yamagishi T-A, Nakamoto Y (2008) Para-bridged symmetrical pillar[5]arenes:
their lewis acid catalyzed synthesis and host–guest property. J Am Chem Soc 130:5022–5023
2. (a) Guo D-S, Liu Y (2014) Supramolecular chemistry of p-sulfonatocalix[n]arenes and its
biological applications. Acc Chem Res 47:1925–1934; (b) Zhao B-T, Zhang H-Y, Liu Y
(2005) Progress on molecular self-assembly based on calixarene derivatives. Chin J Org
Chem 25:913–925
3. (a) Ogoshi T, Hashizume M, Yamagishi T-A, Nakamoto Y (2010) Synthesis, conformational
and hostÀguest properties of water-soluble pillar[5]arene. Chem Commun 46:3708–3710; (b)
Chen Z, Cao D (2010) Synthesis of bis(4-bromo-2,5-dialkoxyphenyl)methane and its
analogues. Chin J Org Chem 30:1742–1744; (c) Ma Y, Zhang Z, Ji X, Han C, He J, Abliz Z,
Chen W, Huang F (2011) Preparation of pillar[n]arenes by cyclooligomerization of 2,5dialkoxybenzyl alcohols or 2,5-dialkoxybenzyl bromides. Eur J Org Chem 2011:5331–5335
4. (a) Han C, Zhang Z, Chi X, Zhang M, Yu G, Huang F (2012) Synthesis of 1,4-bis(n-propoxy)
pillar[7]arene and its host-guest chemistry. Acta Chim Sin 70:1775–1778; (b) Hu X-B, Chen Z,
Chen L, Zhang L, Hou J-L, Li Z-T (2012) Pillar[n]arenes (n = 8–10) with two cavities:
synthesis, structures and complexing properties. Chem Commun 48:10999–11001
5. (a) Li C, Han K, Li J, Zhang H, Ma J, Shu X, Chen Z, Weng L, Jia X (2011) Synthesis of pillar
[5]arene dimers and their cooperative binding toward some neutral guests. Org Lett 14:42–45;
(b) Li C, Ma J, Zhao L, Zhang Y, Yu Y, Shu X, Li J, Jia X (2013) Molecular selective binding of
basic amino acids by a water-soluble pillar[5]arene. Chem Commun 49:1924–1926; (c) Ni M,
Guan Y, Wu L, Deng C, Hu X, Jiang J, Lin C, Wang L (2012) Improved recognition of
alkylammonium salts by ion pair recognition based on a novel heteroditopic pillar[5]arene
receptor. Tetrahedron Lett 53:6409–6413
6. (a) Ogoshi T, Yamagishi T-A (2013) Pillararenes: versatile synthetic receptors for supramolecular chemistry. Eur J Org Chem 2013:2961–2975; (b) Wu X, Duan Q, Ni M, Hu X, Wang L
378
X. Wu et al.
and intrinsically intriguing inclusion properties. Moreover, due to the dynamic
nature of the noncovalent interaction between pillar[n]arene and corresponding
guest molecules, these assemblies exhibited excellent responsiveness to external
stimuli, such as pH, concentration, solvent polarity, temperature, photochemistry,
and competitive components. Therefore, they might have potential application
into the chemical sensors, stimuli-responsive materials, and optical materials.
However, compared to crown ethers, cyclodextrins, calixarenes, and
cucurbiturils, it is still an immature project to build pillararene-based supramolecular
polymers. There are a lot of challenges and opportunities in this emerging research
field. Firstly, although various pillar[n]arene-based supramolecular polymer was
successfully constructed, little efforts had been engaged in the research their properties and applications, especially in the energy and environment fields. Secondly, to
date most researches were conducted in the organic solvent and mainly focused on
the pillar[5]arene and pillar[6]arene, which would limit their potential application in
the biological fields as well as the real life. Finally, how to combine the lab research
with the industrial production was still the barrier to overcome.
References
1. (a) Cao D, Kou Y, Liang J, Chen Z, Wang L, Meier H (2009) A facile and efficient preparation
of pillararenes and a pillarquinone. Angew Chem Int Ed 48:9721–9723; (b) Ogoshi T, Kanai S,
Fujinami S, Yamagishi T-A, Nakamoto Y (2008) Para-bridged symmetrical pillar[5]arenes:
their lewis acid catalyzed synthesis and host–guest property. J Am Chem Soc 130:5022–5023
2. (a) Guo D-S, Liu Y (2014) Supramolecular chemistry of p-sulfonatocalix[n]arenes and its
biological applications. Acc Chem Res 47:1925–1934; (b) Zhao B-T, Zhang H-Y, Liu Y
(2005) Progress on molecular self-assembly based on calixarene derivatives. Chin J Org
Chem 25:913–925
3. (a) Ogoshi T, Hashizume M, Yamagishi T-A, Nakamoto Y (2010) Synthesis, conformational
and hostÀguest properties of water-soluble pillar[5]arene. Chem Commun 46:3708–3710; (b)
Chen Z, Cao D (2010) Synthesis of bis(4-bromo-2,5-dialkoxyphenyl)methane and its
analogues. Chin J Org Chem 30:1742–1744; (c) Ma Y, Zhang Z, Ji X, Han C, He J, Abliz Z,
Chen W, Huang F (2011) Preparation of pillar[n]arenes by cyclooligomerization of 2,5dialkoxybenzyl alcohols or 2,5-dialkoxybenzyl bromides. Eur J Org Chem 2011:5331–5335
4. (a) Han C, Zhang Z, Chi X, Zhang M, Yu G, Huang F (2012) Synthesis of 1,4-bis(n-propoxy)
pillar[7]arene and its host-guest chemistry. Acta Chim Sin 70:1775–1778; (b) Hu X-B, Chen Z,
Chen L, Zhang L, Hou J-L, Li Z-T (2012) Pillar[n]arenes (n = 8–10) with two cavities:
synthesis, structures and complexing properties. Chem Commun 48:10999–11001
5. (a) Li C, Han K, Li J, Zhang H, Ma J, Shu X, Chen Z, Weng L, Jia X (2011) Synthesis of pillar
[5]arene dimers and their cooperative binding toward some neutral guests. Org Lett 14:42–45;
(b) Li C, Ma J, Zhao L, Zhang Y, Yu Y, Shu X, Li J, Jia X (2013) Molecular selective binding of
basic amino acids by a water-soluble pillar[5]arene. Chem Commun 49:1924–1926; (c) Ni M,
Guan Y, Wu L, Deng C, Hu X, Jiang J, Lin C, Wang L (2012) Improved recognition of
alkylammonium salts by ion pair recognition based on a novel heteroditopic pillar[5]arene
receptor. Tetrahedron Lett 53:6409–6413
6. (a) Ogoshi T, Yamagishi T-A (2013) Pillararenes: versatile synthetic receptors for supramolecular chemistry. Eur J Org Chem 2013:2961–2975; (b) Wu X, Duan Q, Ni M, Hu X, Wang L
378
X. Wu et al.