Photocleavage of pyridyl-based aromatic polyureas

Jeremiah Mwaura, Baocheng Yang, Rongfu Li, Martha Morton, Fotios Papadimitrakopoulos

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The photophysical properties of a metal chelating pyridyl-based aromatic ureas and poly-(1,4-phenylene-2,6-pyridylurea) were investigated. In their solution state and upon exposure to 365 nm UV radiation, these low and high molecular weight compounds were found to cleave the urea linkage nearly quantitatively, generating the corresponding amine-terminated subunits and CO2. Through a series of model compounds along with nuclear magnetic resonance (NMR), UV/vis absorption, and fluorescence spectroscopy characterization, the photocleavage process was delinated as a function of UV dose, O2, and water. The presence of water was found crucial to this photocleavage process with O2 playing a role only in subsequent oxidation of resulting amine functionalities. The experimental results support a light-assisted hydrolysis of the urea bond as the most plausible photocleavage mechanism. The photocleavage of such pyridyl-based ureas can potentially find usages in light-assisted base generation and/or for releasing metal cations.

Original languageEnglish (US)
Pages (from-to)9775-9783
Number of pages9
JournalMacromolecules
Volume36
Issue number26
DOIs
StatePublished - Dec 30 2003

Fingerprint

Urea
Amines
Metals
Water
Fluorescence spectroscopy
Chelation
Ultraviolet spectroscopy
Absorption spectroscopy
Ultraviolet radiation
Cations
Hydrolysis
Positive ions
Molecular weight
Nuclear magnetic resonance
Oxidation
polyurea

ASJC Scopus subject areas

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

Cite this

Mwaura, J., Yang, B., Li, R., Morton, M., & Papadimitrakopoulos, F. (2003). Photocleavage of pyridyl-based aromatic polyureas. Macromolecules, 36(26), 9775-9783. https://doi.org/10.1021/ma034058k

Photocleavage of pyridyl-based aromatic polyureas. / Mwaura, Jeremiah; Yang, Baocheng; Li, Rongfu; Morton, Martha; Papadimitrakopoulos, Fotios.

In: Macromolecules, Vol. 36, No. 26, 30.12.2003, p. 9775-9783.

Research output: Contribution to journalArticle

Mwaura, J, Yang, B, Li, R, Morton, M & Papadimitrakopoulos, F 2003, 'Photocleavage of pyridyl-based aromatic polyureas', Macromolecules, vol. 36, no. 26, pp. 9775-9783. https://doi.org/10.1021/ma034058k
Mwaura J, Yang B, Li R, Morton M, Papadimitrakopoulos F. Photocleavage of pyridyl-based aromatic polyureas. Macromolecules. 2003 Dec 30;36(26):9775-9783. https://doi.org/10.1021/ma034058k
Mwaura, Jeremiah ; Yang, Baocheng ; Li, Rongfu ; Morton, Martha ; Papadimitrakopoulos, Fotios. / Photocleavage of pyridyl-based aromatic polyureas. In: Macromolecules. 2003 ; Vol. 36, No. 26. pp. 9775-9783.
@article{c83e2c35e8cf4a208a97f5a121445d8b,
title = "Photocleavage of pyridyl-based aromatic polyureas",
abstract = "The photophysical properties of a metal chelating pyridyl-based aromatic ureas and poly-(1,4-phenylene-2,6-pyridylurea) were investigated. In their solution state and upon exposure to 365 nm UV radiation, these low and high molecular weight compounds were found to cleave the urea linkage nearly quantitatively, generating the corresponding amine-terminated subunits and CO2. Through a series of model compounds along with nuclear magnetic resonance (NMR), UV/vis absorption, and fluorescence spectroscopy characterization, the photocleavage process was delinated as a function of UV dose, O2, and water. The presence of water was found crucial to this photocleavage process with O2 playing a role only in subsequent oxidation of resulting amine functionalities. The experimental results support a light-assisted hydrolysis of the urea bond as the most plausible photocleavage mechanism. The photocleavage of such pyridyl-based ureas can potentially find usages in light-assisted base generation and/or for releasing metal cations.",
author = "Jeremiah Mwaura and Baocheng Yang and Rongfu Li and Martha Morton and Fotios Papadimitrakopoulos",
year = "2003",
month = "12",
day = "30",
doi = "10.1021/ma034058k",
language = "English (US)",
volume = "36",
pages = "9775--9783",
journal = "Macromolecules",
issn = "0024-9297",
publisher = "American Chemical Society",
number = "26",

}

TY - JOUR

T1 - Photocleavage of pyridyl-based aromatic polyureas

AU - Mwaura, Jeremiah

AU - Yang, Baocheng

AU - Li, Rongfu

AU - Morton, Martha

AU - Papadimitrakopoulos, Fotios

PY - 2003/12/30

Y1 - 2003/12/30

N2 - The photophysical properties of a metal chelating pyridyl-based aromatic ureas and poly-(1,4-phenylene-2,6-pyridylurea) were investigated. In their solution state and upon exposure to 365 nm UV radiation, these low and high molecular weight compounds were found to cleave the urea linkage nearly quantitatively, generating the corresponding amine-terminated subunits and CO2. Through a series of model compounds along with nuclear magnetic resonance (NMR), UV/vis absorption, and fluorescence spectroscopy characterization, the photocleavage process was delinated as a function of UV dose, O2, and water. The presence of water was found crucial to this photocleavage process with O2 playing a role only in subsequent oxidation of resulting amine functionalities. The experimental results support a light-assisted hydrolysis of the urea bond as the most plausible photocleavage mechanism. The photocleavage of such pyridyl-based ureas can potentially find usages in light-assisted base generation and/or for releasing metal cations.

AB - The photophysical properties of a metal chelating pyridyl-based aromatic ureas and poly-(1,4-phenylene-2,6-pyridylurea) were investigated. In their solution state and upon exposure to 365 nm UV radiation, these low and high molecular weight compounds were found to cleave the urea linkage nearly quantitatively, generating the corresponding amine-terminated subunits and CO2. Through a series of model compounds along with nuclear magnetic resonance (NMR), UV/vis absorption, and fluorescence spectroscopy characterization, the photocleavage process was delinated as a function of UV dose, O2, and water. The presence of water was found crucial to this photocleavage process with O2 playing a role only in subsequent oxidation of resulting amine functionalities. The experimental results support a light-assisted hydrolysis of the urea bond as the most plausible photocleavage mechanism. The photocleavage of such pyridyl-based ureas can potentially find usages in light-assisted base generation and/or for releasing metal cations.

UR - http://www.scopus.com/inward/record.url?scp=0346687397&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0346687397&partnerID=8YFLogxK

U2 - 10.1021/ma034058k

DO - 10.1021/ma034058k

M3 - Article

AN - SCOPUS:0346687397

VL - 36

SP - 9775

EP - 9783

JO - Macromolecules

JF - Macromolecules

SN - 0024-9297

IS - 26

ER -