PH triggered smart organogel from DCDHF-Hydrazone molecular switch

Tawfik A. Khattab, Brylee David B Tiu, Sonya Adas, Scott D. Bunge, Rigoberto C. Advincula

Research output: Contribution to journalArticle

18 Citations (Scopus)

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 languageEnglish
Pages (from-to)327-336
Number of pages10
JournalDyes and Pigments
Volume130
DOIs
Publication statusPublished - 2016 Jul 1
Externally publishedYes

Fingerprint

Hydrazones
Organic solvents
Bearings (structural)
Switches
Xerogels
X ray crystallography
Propanol
Gelation
Chromophores
Sols
Gases
Self assembly
1-Propanol
Nanostructures
Gels
Molecular weight
Polymethyl Methacrylate
Transmission electron microscopy
Color
Derivatives

Keywords

  • DCDHF-Hydrazone
  • Molecular switch
  • Nanofibers
  • pH-responsive
  • Smart organogel

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Process Chemistry and Technology

Cite this

Khattab, T. A., Tiu, B. D. B., Adas, S., Bunge, S. D., & Advincula, R. C. (2016). PH triggered smart organogel from DCDHF-Hydrazone molecular switch. Dyes and Pigments, 130, 327-336. https://doi.org/10.1016/j.dyepig.2016.03.044

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 journalArticle

Khattab, TA, Tiu, BDB, Adas, S, Bunge, SD & Advincula, RC 2016, 'PH triggered smart organogel from DCDHF-Hydrazone molecular switch', Dyes and Pigments, vol. 130, pp. 327-336. https://doi.org/10.1016/j.dyepig.2016.03.044
Khattab, Tawfik A. ; Tiu, Brylee David B ; Adas, Sonya ; Bunge, Scott D. ; Advincula, Rigoberto C. / PH triggered smart organogel from DCDHF-Hydrazone molecular switch. In: Dyes and Pigments. 2016 ; Vol. 130. pp. 327-336.
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