2004
DOI: 10.1021/ja039515r
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A Condensable Amphiphile with a Cleavable Tail as a “Lizard” Template for the Sol−Gel Synthesis of Functionalized Mesoporous Silica

Abstract: Use of a dialkoxysilane-containing, condensable alanine amphiphile with a cleavable hexadecyl ester tail (1) as a "lizard" template for sol-gel synthesis results in the formation of a mesoporous silicate (2) whose channels are filled with an organic group of the template. Treatment of 2 with aqueous HCl allows selective cleavage of the ester moiety to leave nanochannels (3) whose surface is densely covered with alanine-CO2H. According to XRD and TEM, 2, on conversion into 3, can preserve its regular hexagonal … Show more

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Cited by 147 publications
(113 citation statements)
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“…Organotrialkoxysilanes containing a dimethyl ammonium group as a part of the head group have been reported to generate two-dimensional (2-D) hexagonal and cubic phases in the presence of tetraalkoxysilanes. 20,36,37 However, the synthesis of such mesophases using organosilane precursors having simple hydrocarbon chains still remains a challenge. Recently, the formation of a 2-D hexagonal hybrid from bis(trimethoxysilyl)alkane with a long alkylene spacer was reported.…”
Section: Other Hybrid Mesostructures Obtained By Molecular Designmentioning
confidence: 99%
“…Organotrialkoxysilanes containing a dimethyl ammonium group as a part of the head group have been reported to generate two-dimensional (2-D) hexagonal and cubic phases in the presence of tetraalkoxysilanes. 20,36,37 However, the synthesis of such mesophases using organosilane precursors having simple hydrocarbon chains still remains a challenge. Recently, the formation of a 2-D hexagonal hybrid from bis(trimethoxysilyl)alkane with a long alkylene spacer was reported.…”
Section: Other Hybrid Mesostructures Obtained By Molecular Designmentioning
confidence: 99%
“…331 The organosilane including alanine residue was covalently attached to the silica framework upon solgel reaction with tetraethoxysilane and cleavage and removal of the alkyl tail by selective hydrolysis of the ester at the C-terminal leaves open pores with a surface covalently functionalized by the alanine residue. As one can easily imagine, the template behaves like a "lizard," whose head bites the silica wall and whose tail can be cleaved off.…”
Section: +mentioning
confidence: 99%
“…16) [204][205][206]. A surfactant with condensable alkoxysilane group was used as template in this method.…”
Section: Biomaterial-hybridized Mesoporous Materialsmentioning
confidence: 99%