Photoswitching of Azobenzene-Based Reverse Micelles above and
at Subzero Temperatures As Studied by NMR and Molecular
Dynamics Simulations

J 2017

Photoswitching of Azobenzene-Based Reverse Micelles above and at Subzero Temperatures As Studied by NMR and Molecular Dynamics Simulations

FILIPOVÁ, Lenka, Miriam KOHAGEN, Peter ŠTACKO, Eva MUCHOVA, Petr SLAVÍČEK et. al.

Basic information

Original name

Photoswitching of Azobenzene-Based Reverse Micelles above and at Subzero Temperatures As Studied by NMR and Molecular Dynamics Simulations

Authors

FILIPOVÁ, Lenka (203 Czech Republic, belonging to the institution), Miriam KOHAGEN (276 Germany), Peter ŠTACKO (703 Slovakia, belonging to the institution), Eva MUCHOVA (203 Czech Republic), Petr SLAVÍČEK (203 Czech Republic) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Langmuir, WASHINGTON, AMER CHEMICAL SOC, 2017, 0743-7463

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.789

RIV identification code

RIV/00216224:14310/17:00095284

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.langmuir.6b04455

UT WoS

000395964100026

Keywords in English

IONIC LIQUIDS; FORCE-FIELD; TRANS ISOMERIZATION; DRUG-DELIVERY; WATER; CRYSTALS; LIGHT; PHOTOISOMERIZATION; VESICLES; SOLVENTS

Abstract

V originále

We designed and studied the structure, dynamics, and photochemistry of photoswitchable reverse micelles (RMs) composed of azobenzene-containing ammonium amphiphile 1 and water in chloroform at room and subzero temperatures by NMR spectroscopy and molecular dynamics simulations. The NMR and diffusion coefficient analyses showed that micelles containing either the E or Z configuration of 1 are stable at room temperature. Depending on the water-to-surfactant molar ratio, the size of the RMs remains unchanged or is slightly reduced because of the partial loss of water from the micellar cores upon extensive E -> Z or Z -> E photoisomerization of the azobenzene group in 1. Upon freezing at 253 or 233 K, E-1 RMs partially precipitate from the solution but are redissolved upon warming whereas Z-1 RMs remain fully dissolved at all temperatures. Light-induced isomerization of 1 at low temperatures does not lead to the disintegration of RMs remaining in the solution; however, its scope is influenced by a precipitation process. To obtain a deeper molecular view of RMs, their structure was characterized by MD simulations. It is shown that RMs allow for amphiphile isomerization without causing any immediate significant structural changes in the micelles.

Links

GA15-12386S, research and development project

Name: Dynamika a (foto)chemie polutantů na rozhraních led/vzduch a voda/vzduch z experimentu i teorie

Investor: Czech Science Foundation

LM2015051, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

FILIPOVÁ, Lenka, Miriam KOHAGEN, Peter ŠTACKO, Eva MUCHOVA, Petr SLAVÍČEK and Petr KLÁN. Photoswitching of Azobenzene-Based Reverse Micelles above and at Subzero Temperatures As Studied by NMR and Molecular Dynamics Simulations. Langmuir. WASHINGTON: AMER CHEMICAL SOC, 2017, vol. 33, No 9, p. 2306-2317. ISSN 0743-7463. Available from: https://dx.doi.org/10.1021/acs.langmuir.6b04455.

@article{1400312,
   author = {Filipová, Lenka and Kohagen, Miriam and Štacko, Peter and Muchova, Eva and Slavíček, Petr and Klán, Petr},
   article_location = {WASHINGTON},
   article_number = {9},
   doi = {http://dx.doi.org/10.1021/acs.langmuir.6b04455},
   keywords = {IONIC LIQUIDS; FORCE-FIELD; TRANS ISOMERIZATION; DRUG-DELIVERY; WATER; CRYSTALS; LIGHT; PHOTOISOMERIZATION; VESICLES; SOLVENTS},
   language = {eng},
   issn = {0743-7463},
   journal = {Langmuir},
   title = {Photoswitching of Azobenzene-Based Reverse Micelles above and at Subzero Temperatures As Studied by NMR and Molecular Dynamics Simulations},
   url = {http://pubs.acs.org/doi/10.1021/acs.langmuir.6b04455},
   volume = {33},
   year = {2017}
}

TY  - JOUR
ID  - 1400312
AU  - Filipová, Lenka - Kohagen, Miriam - Štacko, Peter - Muchova, Eva - Slavíček, Petr - Klán, Petr
PY  - 2017
TI  - Photoswitching of Azobenzene-Based Reverse Micelles above and at Subzero Temperatures As Studied by NMR and Molecular Dynamics Simulations
JF  - Langmuir
VL  - 33
IS  - 9
SP  - 2306-2317
EP  - 2306-2317
PB  - AMER CHEMICAL SOC
SN  - 07437463
KW  - IONIC LIQUIDS
KW  - FORCE-FIELD
KW  - TRANS ISOMERIZATION
KW  - DRUG-DELIVERY
KW  - WATER
KW  - CRYSTALS
KW  - LIGHT
KW  - PHOTOISOMERIZATION
KW  - VESICLES
KW  - SOLVENTS
UR  - http://pubs.acs.org/doi/10.1021/acs.langmuir.6b04455
L2  - http://pubs.acs.org/doi/10.1021/acs.langmuir.6b04455
N2  - We designed and studied the structure, dynamics, and photochemistry of photoswitchable reverse micelles (RMs) composed of azobenzene-containing ammonium amphiphile 1 and water in chloroform at room and subzero temperatures by NMR spectroscopy and molecular dynamics simulations. The NMR and diffusion coefficient analyses showed that micelles containing either the E or Z configuration of 1 are stable at room temperature. Depending on the water-to-surfactant molar ratio, the size of the RMs remains unchanged or is slightly reduced because of the partial loss of water from the micellar cores upon extensive E -> Z or Z -> E photoisomerization of the azobenzene group in 1. Upon freezing at 253 or 233 K, E-1 RMs partially precipitate from the solution but are redissolved upon warming whereas Z-1 RMs remain fully dissolved at all temperatures. Light-induced isomerization of 1 at low temperatures does not lead to the disintegration of RMs remaining in the solution; however, its scope is influenced by a precipitation process. To obtain a deeper molecular view of RMs, their structure was characterized by MD simulations. It is shown that RMs allow for amphiphile isomerization without causing any immediate significant structural changes in the micelles.
ER  -

FILIPOVÁ, Lenka, Miriam KOHAGEN, Peter ŠTACKO, Eva MUCHOVA, Petr SLAVÍČEK and Petr KLÁN. Photoswitching of Azobenzene-Based Reverse Micelles above and at Subzero Temperatures As Studied by NMR and Molecular Dynamics Simulations. \textit{Langmuir}. WASHINGTON: AMER CHEMICAL SOC, 2017, vol.~33, No~9, p.~2306-2317. ISSN~0743-7463. Available from: https://dx.doi.org/10.1021/acs.langmuir.6b04455.

Detailed Information on Publication Record