Abstract
The design, synthesis and photophysical properties of a Low Molecular Weight pH-responsive Gelator (LMWG) based on alkoxy group functionalized DCDHF-Hydrazones (DCDHF-H) are described. A straightforward synthesis of DCDHF-Hydrazone (DCDHF-H) chromophores was achieved via simple azo-coupling starting from 2-(dicyanomethylene)-2,5-dihydro-4,5,5-trimethylfuran-3-carbonitrile and alkoxy bearing aryl diazonium chloride derivatives. The DCDHF-H efficiently gelate selected organic solvents and reversibly respond to pH stimuli with a gel-sol conversion and an associated color change from yellow to purple. Self-assembly of these molecules, as indicated by X-ray crystallography, occurs via cooperative π-π stacking and van der Waals interactions producing gelation in some pure and mixed organic solvents. Furthermore, the presence of acidic or alkaline gases leads to a dramatic change in the rheological properties with potential applications in areas such as gas detection devices and drug release systems. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) studies of the xerogels obtained from n-propanol provide visual images revealing the formation of fibrous nanostructures.
| Original language | English |
|---|---|
| Pages (from-to) | 327-336 |
| Number of pages | 10 |
| Journal | Dyes and Pigments |
| Volume | 130 |
| DOIs | |
| Publication status | Published - 2016 Jul 1 |
| Externally published | Yes |
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Keywords
- DCDHF-Hydrazone
- Molecular switch
- Nanofibers
- pH-responsive
- Smart organogel
ASJC Scopus subject areas
- Chemical Engineering(all)
- Process Chemistry and Technology
Cite this
PH triggered smart organogel from DCDHF-Hydrazone molecular switch. / Khattab, Tawfik A.; Tiu, Brylee David B; Adas, Sonya; Bunge, Scott D.; Advincula, Rigoberto C.
In: Dyes and Pigments, Vol. 130, 01.07.2016, p. 327-336.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - PH triggered smart organogel from DCDHF-Hydrazone molecular switch
AU - Khattab, Tawfik A.
AU - Tiu, Brylee David B
AU - Adas, Sonya
AU - Bunge, Scott D.
AU - Advincula, Rigoberto C.
PY - 2016/7/1
Y1 - 2016/7/1
N2 - The design, synthesis and photophysical properties of a Low Molecular Weight pH-responsive Gelator (LMWG) based on alkoxy group functionalized DCDHF-Hydrazones (DCDHF-H) are described. A straightforward synthesis of DCDHF-Hydrazone (DCDHF-H) chromophores was achieved via simple azo-coupling starting from 2-(dicyanomethylene)-2,5-dihydro-4,5,5-trimethylfuran-3-carbonitrile and alkoxy bearing aryl diazonium chloride derivatives. The DCDHF-H efficiently gelate selected organic solvents and reversibly respond to pH stimuli with a gel-sol conversion and an associated color change from yellow to purple. Self-assembly of these molecules, as indicated by X-ray crystallography, occurs via cooperative π-π stacking and van der Waals interactions producing gelation in some pure and mixed organic solvents. Furthermore, the presence of acidic or alkaline gases leads to a dramatic change in the rheological properties with potential applications in areas such as gas detection devices and drug release systems. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) studies of the xerogels obtained from n-propanol provide visual images revealing the formation of fibrous nanostructures.
AB - The design, synthesis and photophysical properties of a Low Molecular Weight pH-responsive Gelator (LMWG) based on alkoxy group functionalized DCDHF-Hydrazones (DCDHF-H) are described. A straightforward synthesis of DCDHF-Hydrazone (DCDHF-H) chromophores was achieved via simple azo-coupling starting from 2-(dicyanomethylene)-2,5-dihydro-4,5,5-trimethylfuran-3-carbonitrile and alkoxy bearing aryl diazonium chloride derivatives. The DCDHF-H efficiently gelate selected organic solvents and reversibly respond to pH stimuli with a gel-sol conversion and an associated color change from yellow to purple. Self-assembly of these molecules, as indicated by X-ray crystallography, occurs via cooperative π-π stacking and van der Waals interactions producing gelation in some pure and mixed organic solvents. Furthermore, the presence of acidic or alkaline gases leads to a dramatic change in the rheological properties with potential applications in areas such as gas detection devices and drug release systems. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) studies of the xerogels obtained from n-propanol provide visual images revealing the formation of fibrous nanostructures.
KW - DCDHF-Hydrazone
KW - Molecular switch
KW - Nanofibers
KW - pH-responsive
KW - Smart organogel
UR - http://www.scopus.com/inward/record.url?scp=84962018375&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84962018375&partnerID=8YFLogxK
U2 - 10.1016/j.dyepig.2016.03.044
DO - 10.1016/j.dyepig.2016.03.044
M3 - Article
VL - 130
SP - 327
EP - 336
JO - Dyes and Pigments
JF - Dyes and Pigments
SN - 0143-7208
ER -