Journal of Molecular Structure, volume 1234, pages 130127

Synthesis and organogelating behaviour of urea- and Fmoc-containing diphenylalanine based hexaamide

Machulkin Aleksei E. ¹

Petrov Stanislav B. ¹

Tavtorkin Alexander N. ²

Bondarenko Galina N. ²

Legkov Sergey A ²

Nifant'ev Ilya E. ^{2, 3}

Dolzhikova Valentina D ¹

Zyk Nikolay V. ¹

Majouga Alexander G. ^{4, 5, 6}

Beloglazkina Elena K. ¹

Hide authors affiliations Show authors affiliations: 6 affiliations

Lomonosov Moscow State University, Chemistry Dept, Leninskie gory, Building 1/3, GSP-1, Moscow, 119991. Russian Federation. |

A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Leninskiy pr, Building 29/2, Moscow, 119991, Russian Federation. |

Lomonosov Moscow State University, Chemistry Dept., Leninskie gory, Building 1/3, GSP-1, Moscow, 119991, Russian Federation. |

⁴

Dmitry Mendeleev University of Chemical Technology of Russia, Miusskaya Sq. 9, Moscow, 125047, Russian Federation |

⁵

Lomonosov Moscow State University, Chemistry Dept., Leninskie Gory, Building 1/3, GSP-1, Moscow, 119991, Russian Federation |

⁶

National University of Science and Technology MISiS, 9 Leninskiy pr, Moscow 119049, Russian Federation |

Publication type: Journal Article

Publication date: 2021-06-01

Elsevier

Journal: Journal of Molecular Structure

Quartile SCImago

Quartile WOS

Impact factor: 3.8

ISSN: 00222860

DOI: 10.1016/j.molstruc.2021.130127

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Organic Chemistry

Inorganic Chemistry

Spectroscopy

Analytical Chemistry

Abstract

Abstract A new low molecular mass organic gelator based on tri-tert-butylates Glu-Urea-Lys and Fmoc-capped di-L-Phe-containing hexaamide (tri-tert-butyl (10S,13S,31S,35S)-10,13-dibenzyl-1-(9H-fluoren-9-yl)-3,9,12,15,18,25,33-heptaoxo-2-oxa-4,8,11,14,19,26,32,34-octaazaheptatriacontane-31,35,37-tricarboxylate, 9) was synthesized and examined for the ability to gelate various organic solvents (dichloromethane (DCM), chlorophorm, methanol, acetonitrile and acetonitrile/water mixtures, ethyl acetate). The microstructure of the obtained gels was studied using scanning electron microscopy (SEM). It was shown that the morphologies of the xerogels, formed by the slow drying of the corresponding organogels, differ for different solvents. For example, xerogels from DCM showed the layered slab structures with widths and lengths to hundreds of micrometers, but xerogels in ethanol exhibit networks composed of entwined fibers. Based on FTIR, 1H NMR and UV-vis data, the gelator molecules are aggregate via N–H/O hydrogen bonding, hydrophobic interaction and π-π-staking.

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Machulkin A. E. et al. Synthesis and organogelating behaviour of urea- and Fmoc-containing diphenylalanine based hexaamide // Journal of Molecular Structure. 2021. Vol. 1234. p. 130127.

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Machulkin A. E., Petrov S. B., Tavtorkin A. N., Bondarenko G. N., Legkov S. A., Nifant'ev I. E., Dolzhikova V. D., Zyk N. V., Majouga A. G., Beloglazkina E. K. Synthesis and organogelating behaviour of urea- and Fmoc-containing diphenylalanine based hexaamide // Journal of Molecular Structure. 2021. Vol. 1234. p. 130127.

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RIS Copy

TY - JOUR

DO - 10.1016/j.molstruc.2021.130127

UR - https://doi.org/10.1016%2Fj.molstruc.2021.130127

TI - Synthesis and organogelating behaviour of urea- and Fmoc-containing diphenylalanine based hexaamide

T2 - Journal of Molecular Structure

AU - Petrov, Stanislav B.

AU - Machulkin, Aleksei E.

AU - Tavtorkin, Alexander N.

AU - Bondarenko, Galina N.

AU - Legkov, Sergey A

AU - Nifant'ev, Ilya E.

AU - Dolzhikova, Valentina D

AU - Zyk, Nikolay V.

AU - Majouga, Alexander G.

AU - Beloglazkina, Elena K.

PY - 2021

DA - 2021/06/01 00:00:00

PB - Elsevier

SP - 130127

VL - 1234

SN - 0022-2860

ER -

BibTex

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BibTex Copy

@article{2021_Machulkin,

author = {Stanislav B. Petrov and Aleksei E. Machulkin and Alexander N. Tavtorkin and Galina N. Bondarenko and Sergey A Legkov and Ilya E. Nifant'ev and Valentina D Dolzhikova and Nikolay V. Zyk and Alexander G. Majouga and Elena K. Beloglazkina},

title = {Synthesis and organogelating behaviour of urea- and Fmoc-containing diphenylalanine based hexaamide},

journal = {Journal of Molecular Structure},

year = {2021},

volume = {1234},

publisher = {Elsevier},

month = {jun},

url = {https://doi.org/10.1016%2Fj.molstruc.2021.130127},

pages = {130127},

doi = {10.1016/j.molstruc.2021.130127}

}

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Publisher

Elsevier

Journal

Journal of Molecular Structure

Quartile SCImago

Quartile WOS

Impact factor

3.8

ISSN

00222860 (Print)

Labs

Laboratory of Biologically Active Organic Compounds (BAOС)

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