Photoswitchable nanocarrier with reversible encapsulation properties

Peng Fei Cao, Zhe Su, Al De Leon, Rigoberto C. Advincula

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

An amphiphilic dendritic polymer with polyethylenimine (PEI) as the hydrophilic core, steric ester (STA) as the hydrophobic shell, and azobenzene (AZO) groups as the photoswitchable moieties was synthesized via amidation reaction. The synthesized dendritic macromolecule was characterized by 1H nuclear magnetic resonance (NMR), FT-IR spectroscopy, and dynamic light scattering (DLS). With alternating UV and visible-light irradiation, azobenzene moieties of polyethylenimine-steric ester-azobenzene (PEI-STA-AZO) undergo a reversible isomerization between the cis and trans state. The encapsulation tests demonstrated that PEI-STA-AZO with trans-isomer is not capable of encapsulating anionic guests, whereas the one with cis-isomers is able to encapsulate the anionic guests from the aqueous solution to the organic layer. Molecular modeling by Spartan was utilized to explain the special encapsulation property of PEI-STA-AZO. Azobenzene groups functioned as a reversible "photo-switch" in the dendritic guest-host system, and the reversibility of encapsulation capability of PEI-STA-AZO was also demonstrated. (Figure Presented).

Original languageEnglish
Pages (from-to)58-62
Number of pages5
JournalACS Macro Letters
Volume4
Issue number1
DOIs
Publication statusPublished - 2015
Externally publishedYes

Fingerprint

Azobenzene
Encapsulation
Polyethyleneimine
Isomers
Esters
Magnetic resonance spectroscopy
Dendrimers
Molecular modeling
azobenzene
Dynamic light scattering
Isomerization
Macromolecules
Infrared spectroscopy
Switches
Nuclear magnetic resonance
Irradiation

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Photoswitchable nanocarrier with reversible encapsulation properties. / Cao, Peng Fei; Su, Zhe; De Leon, Al; Advincula, Rigoberto C.

In: ACS Macro Letters, Vol. 4, No. 1, 2015, p. 58-62.

Research output: Contribution to journalArticle

Cao, PF, Su, Z, De Leon, A & Advincula, RC 2015, 'Photoswitchable nanocarrier with reversible encapsulation properties', ACS Macro Letters, vol. 4, no. 1, pp. 58-62. https://doi.org/10.1021/mz500632r
Cao, Peng Fei ; Su, Zhe ; De Leon, Al ; Advincula, Rigoberto C. / Photoswitchable nanocarrier with reversible encapsulation properties. In: ACS Macro Letters. 2015 ; Vol. 4, No. 1. pp. 58-62.
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AB - An amphiphilic dendritic polymer with polyethylenimine (PEI) as the hydrophilic core, steric ester (STA) as the hydrophobic shell, and azobenzene (AZO) groups as the photoswitchable moieties was synthesized via amidation reaction. The synthesized dendritic macromolecule was characterized by 1H nuclear magnetic resonance (NMR), FT-IR spectroscopy, and dynamic light scattering (DLS). With alternating UV and visible-light irradiation, azobenzene moieties of polyethylenimine-steric ester-azobenzene (PEI-STA-AZO) undergo a reversible isomerization between the cis and trans state. The encapsulation tests demonstrated that PEI-STA-AZO with trans-isomer is not capable of encapsulating anionic guests, whereas the one with cis-isomers is able to encapsulate the anionic guests from the aqueous solution to the organic layer. Molecular modeling by Spartan was utilized to explain the special encapsulation property of PEI-STA-AZO. Azobenzene groups functioned as a reversible "photo-switch" in the dendritic guest-host system, and the reversibility of encapsulation capability of PEI-STA-AZO was also demonstrated. (Figure Presented).

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