Bolaamphiphiles Bearing Bipyridine as Mesogenic Core: Rational Exploitation of Molecular Architectures for Controlled Self-Assembly
- Guanglu Wu ,
- Peter Verwilst ,
- Jun Xu ,
- Huaping Xu ,
- Ruji Wang ,
- Mario Smet ,
- Wim Dehaen ,
- Charl F. J. Faul ,
- Zhiqiang Wang , and
- Xi Zhang
Abstract

A bolaamphiphile (5,5-B2NBr8) bearing a functional bipyridine moiety as the mesogenic core is reported for the first time. 5,5-B2NBr8 was found to self-assemble into uniform fibrous structure in aqueous solution, when the concentration was higher than cmc. Analogues of 5,5-B2NBr8 with structural differences in chain length, headgroup, mesogenic core, and substituted position were synthesized, elucidating that small variances of the molecular structure could lead to dramatic changes of the resulting assemblies. For example, compound 4,4-B2NBr8 showed only spherical colloidal aggregates rather than fibers as 5,5-B2NBr8 did, while the only difference between them was the position at which the alkyl chains were attached onto bipyridine. A probable model for the fibrous structure of 5,5-B2NBr8 was proposed. Moreover, exploiting the coordination capacity of bipyridine, assembly and disassembly of 5,5-B2NBr8 could be reversibly controlled through the addition of EDTA and Cu(II), respectively.
Cited By
This article is cited by 24 publications.
- Xuewen Du, Jie Zhou, Junfeng Shi, and Bing Xu . Supramolecular Hydrogelators and Hydrogels: From Soft Matter to Molecular Biomaterials. Chemical Reviews 2015, 115 (24) , 13165-13307. https://doi.org/10.1021/acs.chemrev.5b00299
- Liulin Yang, Hui Yang, Fei Li, and Xi Zhang . Supramolecular Glycolipid Based on Host-Enhanced Charge Transfer Interaction. Langmuir 2013, 29 (40) , 12375-12379. https://doi.org/10.1021/la402973g
- Jun Xu, Guanglu Wu, Zhiqiang Wang, and Xi Zhang . Growth Mechanisms of 2D Organic Assemblies Generated from Dialkylated Melaminium Derivatives: The Length Difference of the Two Alkyl Chains That Matters. Langmuir 2013, 29 (34) , 10959-10963. https://doi.org/10.1021/la402622j
- Xinhua Huang, Young-Il Jeong, Byeong Kyu Moon, Lidong Zhang, Dae Hwan Kang, and Il Kim . Self-Assembly of Morphology-Tunable Architectures from Tetraarylmethane Derivatives for Targeted Drug Delivery. Langmuir 2013, 29 (10) , 3223-3233. https://doi.org/10.1021/la305069e
- Guangtong Wang, Chao Wang, Zhiqiang Wang, and Xi Zhang . H-Shaped Supra-Amphiphiles Based on a Dynamic Covalent Bond. Langmuir 2012, 28 (41) , 14567-14572. https://doi.org/10.1021/la303272b
- Dmitry S. Kopchuk, Ekaterina S. Starnovskaya, Yaroslav K. Shtaitz, Maria I. Savchuk, Alexey P. Krinochkin, Grigory V. Zyryanov, Vladimir L. Rusinov, Oleg N. Chupakhin. Convenient synthetic approach towards high alcohol esters of 5-aryl-2,2′-bipyridine-5′-carboxylic acids. 2020,,, 040023. https://doi.org/10.1063/5.0018677
- Na Zhang, Taisheng Wang, Xiaohai Bu, Qiong Wu, Zewu Zhang. Preparation of few‐layer two‐dimensional polymers by self‐assembly of bola‐amphiphilic small molecules. Journal of Polymer Science Part A: Polymer Chemistry 2019, 57 (16) , 1748-1755. https://doi.org/10.1002/pola.29444
- Nabila Mehwish, Xiaoqiu Dou, Chuanliang Feng. Trends in design of C2-symmetric supramolecular chiral gelators. European Polymer Journal 2019, 117 , 236-253. https://doi.org/10.1016/j.eurpolymj.2019.05.034
- S.R. Ede, S. Anantharaj, K. Sakthikumar, K. Karthick, Subrata Kundu. Investigation of various synthetic protocols for self-assembled nanomaterials and their role in catalysis: progress and perspectives. Materials Today Chemistry 2018, 10 , 31-78. https://doi.org/10.1016/j.mtchem.2018.07.003
- Huan Yao, Liu-Pan Yang, Xin-Yu Pang, Jia-Rong Li, Wei Jiang. Self-assembly of two-dimensional structures in water from rigid and curved amphiphiles with a low molecular weight. Chemical Communications 2018, 54 (77) , 10847-10850. https://doi.org/10.1039/C8CC04570D
- Jun Hu, Lei Gao, Youliang Zhu, Peiyi Wang, Yuan Lin, Zhaoyan Sun, Song Yang, Qian Wang. Chiral Assemblies from an Achiral Pyridinium-Tailored Anthracene. Chemistry - A European Journal 2017, 23 (6) , 1422-1426. https://doi.org/10.1002/chem.201604730
- Junyao Yao, Qibin Chen, Yujie Sheng, Aiting Kai, Honglai Liu. pH-controlled crystal growth of copper/gemini surfactant complexes with bipyridine groups. CrystEngComm 2017, 19 (39) , 5835-5843. https://doi.org/10.1039/C7CE01251A
- Jiao Wang, Meihuan Yao, Qintang Li, Sijing Yi, Xiao Chen. β-Cyclodextrin induced hierarchical self-assembly of a cationic surfactant bearing an adamantane end group in aqueous solution. Soft Matter 2016, 12 (48) , 9641-9648. https://doi.org/10.1039/C6SM02329K
- Yujie Sheng, Qibin Chen, Junyao Yao, Ying Wang, Honglai Liu. Hierarchical Assembly of a Dual-responsive Macroscopic Insulated Molecular Wire Bundle in a Gradient System. Scientific Reports 2015, 5 (1) https://doi.org/10.1038/srep07791
- Qibin Chen, Junyao Yao, Xin Hu, Jincheng Shen, Yujie Sheng, Honglai Liu. Monolayer effect of a gemini surfactant with a rigid biphenyl spacer on its self-crystallization at the air/liquid interface. Journal of Applied Crystallography 2015, 48 (3) , 728-735. https://doi.org/10.1107/S1600576715004938
- Yingzhi Jin, Yijun Xia, Shuai Wang, Li Yan, Yi Zhou, Jian Fan, Bo Song. Concentration-dependent and light-responsive self-assembly of bolaamphiphiles bearing α-cyanostilbene based photochromophore. Soft Matter 2015, 11 (4) , 798-805. https://doi.org/10.1039/C4SM02392G
- Nolwenn Terme, Alicia Jacquemet, Thierry Benvegnu, Véronique Vié, Loïc Lemiègre. Modification of bipolar lipid conformation at the air/water interface by a single stereochemical variation. Chemistry and Physics of Lipids 2014, 183 , 9-17. https://doi.org/10.1016/j.chemphyslip.2014.04.008
- Guanglu Wu, Joice Thomas, Mario Smet, Zhiqiang Wang, Xi Zhang. Controlling the self-assembly of cationic bolaamphiphiles: hydrotropic counteranions determine aggregated structures. Chem. Sci. 2014, 5 (8) , 3267-3274. https://doi.org/10.1039/C4SC00860J
- Subhasish Roy, Dibakar Kumar Maiti, Shrabani Panigrahi, Durga Basak, Arindam Banerjee. A bolaamphiphilic amino acid appended photo-switching supramolecular gel and tuning of photo-switching behaviour. Physical Chemistry Chemical Physics 2014, 16 (13) , 6041. https://doi.org/10.1039/c3cp55108c
- Jinlong Huang, Shuai Wang, Guanglu Wu, Li Yan, Lin Dong, Xiaoping Lai, Shouchun Yin, Bo Song. Mono-molecule-layer nano-ribbons formed by self-assembly of bolaamphiphiles. Soft Matter 2014, 10 (7) , 1018. https://doi.org/10.1039/c3sm52365a
- Guanglu Wu, Peter Verwilst, Kai Liu, Mario Smet, Charl F. J. Faul, Xi Zhang. Controlling the self-assembly of cationic bolaamphiphiles: counterion-directed transitions from 0D/1D to exclusively 2D planar structures. Chemical Science 2013, 4 (12) , 4486. https://doi.org/10.1039/c3sc52342j
- Simon Drescher, Stefan Sonnenberger, Annette Meister, Alfred Blume, Bodo Dobner. Synthesis of symmetrical, single-chain, phenylene/biphenylene-modified bolaamphiphiles. Monatshefte für Chemie - Chemical Monthly 2012, 143 (11) , 1533-1543. https://doi.org/10.1007/s00706-012-0833-2
- Brian Patrick, Jennifer Yeh, Jeremy Comba, Eric M. Everett, Kallum Koczkur, Michael D. Pungente. Synthesis and characterization of macrocyclic bisphosphonate dimers. QScience Connect 2012, 2 (2012) , 10. https://doi.org/10.5339/connect.2012.10
- Steve Landsmann, Martin Luka, Sebastian Polarz. Bolaform surfactants with polyoxometalate head groups and their assembly into ultra-small monolayer membrane vesicles. Nature Communications 2012, 3 (1) https://doi.org/10.1038/ncomms2321



