Bolaamphiphiles (also known as ''bolaform surfactants'',
''bolaphiles'', or ''alpha-omega-type surfactants'') are
amphiphilic
An amphiphile (from the Greek αμφις amphis, both, and φιλíα philia, love, friendship), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'') properties. Such a compo ...
molecules that have
hydrophilic
A hydrophile is a molecule or other molecular entity that is attracted to water molecules and tends to be dissolved by water.Liddell, H.G. & Scott, R. (1940). ''A Greek-English Lexicon'' Oxford: Clarendon Press.
In contrast, hydrophobes are ...
groups at both ends of a sufficiently long
hydrophobic
In chemistry, hydrophobicity is the physical property of a molecule that is seemingly repelled from a mass of water (known as a hydrophobe). In contrast, hydrophiles are attracted to water.
Hydrophobic molecules tend to be nonpolar and, t ...
hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
chain. Compared to single-headed
amphiphiles, the introduction of a second head-group generally induces a higher solubility in water, an increase in the
critical micelle concentration
In colloidal and surface chemistry, the critical micelle concentration (CMC) is defined as the concentration of surfactants above which micelles form and all additional surfactants added to the system will form micelles.
The CMC is an important c ...
(cmc), and a decrease in aggregation number. The aggregate morphologies of bolaamphiphiles include spheres, cylinders, disks, and vesicles. Bolaamphiphiles are also known to form helical structures that can form monolayer microtubular self-assemblies.
[P/ Mosae Selvakumar et al, J. Mol. Struct. 919 (2009) 72-78]
References
* Fuhrhop, J-H; Wang, T. Bolaamphiphile, Chem. Rev. (2004), 104(6), 2901-2937.
* Chen, Yuxia; Liu, Yan; Guo, Rong. Aggregation behavior of an amino acid-derived bolaamphiphile and a conventional surfactant mixed system. Journal of Colloid and Interface Science (2009), 336(2), 766-772. CODEN: JCISA5 . AN 2009:776584
* Yin, Shouchun; Wang, Chao; Song, Bo; Chen, Senlin; Wang, Zhiqiang. Self-Organization of a Polymerizable Bolaamphiphile Bearing a Diacetylene Group and L-Aspartic Acid Group. Langmuir (2009), 25(16), 8968-8973. CODEN: LANGD5 . CAN 151:173915 AN 2009:383258
* Wang, H.; Li, M.; Xu, Z.; Qiao, W.; Li, Z. Interfacial tension of unsymmetrical bolaamphiphile surfactant in surfactant/alkali/crude oil systems. Energy Sources, Part A: Recovery, Utilization, and Environmental Effects (2008), 30(16), 1442-1450. CODEN: ESPACB . CAN 150:475745 AN 2008:763292
* Chen, Senlin; Song, Bo; Wang, Zhiqiang; Zhang, Xi. Self-Organization of Bolaamphiphile Bearing Biphenyl Mesogen and Aspartic-Acid Headgroups. Journal of Physical Chemistry C (2008), 112(9), 3308-3313. CODEN: JPCCCK . CAN 148:372219 AN 2008:176360
* Feng Qiu, Chengkang Tang, Yongzhu Chen Amyloid-like aggregation of designer bolaamphiphilic peptides: Effect of hydrophobic section and hydrophilic heads. Journal of peptide science. (2017) DOI: 10.1002/psc.3062
Organic chemistry
Physical chemistry
Surfactants
{{chemistry-stub