PMID- 34791874
OWN - NLM
STAT- MEDLINE
DCOM- 20220127
LR  - 20220127
IS  - 1520-5827 (Electronic)
IS  - 0743-7463 (Linking)
VI  - 37
IP  - 47
DP  - 2021 Nov 30
TI  - Synthesis and Characterization of a Pyrene-Labeled Gemini Surfactant Sensitive to 
      the Polarity of Its Environment.
PG  - 13824-13837
LID - 10.1021/acs.langmuir.1c01759 [doi]
AB  - The cationic gemini surfactant PyO-3-12 was designed to include two dimethyl 
      ammonium groups, one dodecyl tail, and 1-pyrenemethyl hexyl ether tail into the 
      structure of the surfactant. The pyrenyl label ensured that the fluorescence of 
      pyrene could be employed to probe the behavior of PyO-3-12 at the molecular 
      level. The introduction of the oxygen atom in the beta-position to pyrene was found 
      to be critical for restoring the sensitivity of the pyrenyl label to the polarity 
      of its environment. The properties of PyO-3-12 were characterized in water by 
      surface tension and a fluorescence methodology that involved the global 
      model-free analysis (MFA) of the pyrene monomer and excimer fluorescence decays 
      to provide quantitative information about the state (unassociated-vs-aggregated) 
      of PyO-3-12. The MFA was combined with a fluorescence quenching study with 
      2,6-dinitrotoluene to determine the size of the PyO-3-12 micelles. PyO-3-12 was 
      found to behave like a typical gemini surfactant, exhibiting a critical micelle 
      concentration (CMC) of 0.38 (+/-0.05) mM and an aggregation number (N(agg)) equal 
      to 23 (+/-2). Besides allowing PyO-3-12 to probe the polarity of its environment, 
      the oxygen atom in the beta-position next to pyrene brought some pyrenyl labels 
      closer to the interface between the micellar interior and the aqueous phase, in a 
      process that increased the effective volume of the hydrophobic part of PyO-3-12. 
      This led to an increase in the packing parameter of PyO-3-12 and, consequently, 
      an increase in N(agg) compared to the N(agg) value of 14 (+/-0.2) obtained for 
      Py-3-12, a gemini surfactant, whose chemical structure was similar to that of 
      PyO-3-12 but without the oxygen in the beta-position to pyrene. The methodology 
      described in this study to prepare and characterize pyrene-labeled surfactants is 
      general and can be applied to study any pyrene-labeled surfactant and its 
      interactions with oppositely charged macromolecules.
FAU - Ba-Salem, Abdullah O
AU  - Ba-Salem AO
AD  - Institute for Polymer Research, Waterloo Institute for Nanotechnology, Department 
      of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1.
FAU - Duhamel, Jean
AU  - Duhamel J
AUID- ORCID: 0000-0002-7575-2990
AD  - Institute for Polymer Research, Waterloo Institute for Nanotechnology, Department 
      of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20211118
PL  - United States
TA  - Langmuir
JT  - Langmuir : the ACS journal of surfaces and colloids
JID - 9882736
RN  - 0 (Micelles)
RN  - 0 (Pyrenes)
RN  - 0 (Surface-Active Agents)
SB  - IM
MH  - Hydrophobic and Hydrophilic Interactions
MH  - Micelles
MH  - *Pyrenes
MH  - Surface Tension
MH  - *Surface-Active Agents
EDAT- 2021/11/19 06:00
MHDA- 2022/01/28 06:00
CRDT- 2021/11/18 08:40
PHST- 2021/11/19 06:00 [pubmed]
PHST- 2022/01/28 06:00 [medline]
PHST- 2021/11/18 08:40 [entrez]
AID - 10.1021/acs.langmuir.1c01759 [doi]
PST - ppublish
SO  - Langmuir. 2021 Nov 30;37(47):13824-13837. doi: 10.1021/acs.langmuir.1c01759. Epub 
      2021 Nov 18.