Oleg Kulikov Research Summary 2016-short

PhD Oleg V. Kulikov Research Summary ([email protected])

POLYMERS CHEMISTRY & PDA NANO-TUBES

UT Dallas, Chemistry Department, Richardson, TX, with Profs. Bruce Novak and Ray Baughman

(2013-current)

Project 1: TMAFM/SEM inspection of the fibrous aggregated morphologies and other complex architectures self-

assembled from helical (R)-and (S)-triazolepolycarbodiimides

Project 2: Copolymerization of triazole-functionalized carbodiimides (R- and S-) with styrene

1). R-50-TRZinsol.

-50-Ph-STYR(1:50)-DMF, 90-95o

C;

2). R-50-TRZinsol.

-50-Ph-STYR(1:100)-DMF, 90-95o

C;

3). S-30-TRZinsol.

-70-Ph-STYR(1:100)-DMF, 90-95o

C;

4). S-30-TRZinsol.

-70-Ph-STYR(1:50)-DMF, 90-95o

C;

5). S-30-TRZinsol.

-70-Ph-STYR(1:100)-DMF, 90-95o

C;

6). S-85-TRZ-15-Ph-STYR(1:50)-DMF, 90-95o

C;

7). S-85-TRZ-15-Ph-STYR(1:100)-DMF, 90-95o

C;

8). S-70-TRZ-30-Ph-STYR(1:50)-DMF, 90-95o

C;

9). S-100-TRZ-STYR(1:50)-toluene, 90-95o

C;

10). S-100-TRZ-STYR(1:50)-DMF, 80-82o

C;

11). S-70-TRZ-30-Ph-STYR(1:50)-DMF, 90-95o

C;

12). R-50-TRZ-50-Ph-STYR(1:50)-DMF, 90-95o

C;

13). R-50-TRZ-50-Ph-STYR(1:50)-toluene, 95o

C;

14). S-50-TRZ-50-Ph-STYR(1:50)-toluene, 95o

C;

15). S-30-TRZsol.

-70-Ph-STYR(1:50)-toluene, 84-92o

C;

16). R-30-TRZsol.

-70-Ph-STYR(1:50)-toluene, 90-100o

C;

17). R-30-TRZinsol.

-70-Ph-STYR(1:50)-toluene, 90-95o

C;

18). R-30-TRZsol.

-70-Ph-STYR(1:50)-DMF, 95o

C;

19). R-30-TRZinsol.

-70-Ph-STYR(1:50)-DMF, 90-95o

C;

20). R-15-TRZsol.

-85-Ph-STYR(1:100)-DMF, 90-95o

C;

21). S-15-TRZsol.

-85-Ph-STYR(1:100)-DMF, 90-95o

C;

22). R-15-TRZsol.

-85-Ph-STYR(1:50)-DMF, 90-95o

C;

23). S-15-TRZsol.

-85-Ph-STYR(1:50)-DMF, 90-95o

C;

24). R-15-TRZsol.

-85-Ph-STYR(1:50)-DMF, 63-67o

C,1d;

25). S-15-TRZsol.

-85-Ph-STYR(1:50)-DMF, 63-72o

C,1d;

26). S-30-TRZsol.

-70-Ph-STYR(1:50)-DMF, 60-62o

C,1d;

27). R-30-TRZsol.

-70-Ph-STYR(1:50)-DMF, 57-65o

C,6hr;

28). R-85-TRZsol.

-15-Ph-STYR(1:50)-DMF, 55-60o

C,6hr;

29). R-85-TRZsol.

-15-Ph-STYR(1:50)-DMF, 55-60o

C,1d

Polymer morphological studies and molecular modeling

Project 3: Synthesis of diacetylenes and their transformation to the ladder-type polymers

UV-induced polymerization

BIOORGANIC/SUPRAMOLEULAR CHEMISTRY

University of Pennsylvania, Chemistry Department, Philadelphia, PA, with Prof. Virgil Percec (2012)

Project: Dendritic molecules – synthesis of Janus dendrimers via modular protocol, modeling studies,

formation of vesicles for the protein binding applications

MEDICINAL CHEMISTRY

Yale University, Chemistry Department, New Haven, CT, with Prof. Andrew Hamilton (2009-2011)

Project 1: Novel non-natural oligoamides as potential alpha-helix mimetics

Vesicles self-assembly in aqueous media

Canonical α-helix with side chain residues and proposed benzamide trimer to target RhoGEF domain

control of compounds alone and inhibition of 10 uM hIAPP toxicity (hIAPP:compound, 1:1)

Project 2: Design and synthesis of oligoamide-based double alpha-helix mimetics

Schematic representation of double helix mimetic with side chains (a) and protein double alpha helix (b)

MACROCYCLIC/BIOORGANIC/SUPRAMOLEULAR CHEMISTRY

UMSL, Chemistry Department, St. Louis, MO with Prof. George Gokel (2007-2009)

Project: Supramolecular nano-capsules, metal organic nano-capsules (MONCS), “bilayers” and nano-

tubes derived from pyrogallol[4]arenes for drug delivery and ion transport applications

Cu-MONC`s

R = Me, C3H7, C6H13, C8H17 – C13H27, CH2=CH-(CH2)8-,

cyclohexyl-, Ph, p-C6H4Br, isopropyl-, 2-butyl-, 3-pentyl,

4-heptyl-, 5-nonyl-, 2-pentyl-, 3-heptyl

Ion-conducting properties of capsules and nano-tubular arrangements

Cu-MONC`s

Small drug molecules such as Diazepam (magenta) may be captured within hydrophobic pockets formed by long aliphatic chains of capsule and then released (enzymatic or photochemical mechanism)

MACROCYCLIC CHEMISTRY

NCSU, Chemistry Department, Raleigh, NC with Prof. Jonathan Lindsey (2006-2007)

Project: “Molecular Information Storage” – developing porphyrins for molecular electronic applications

SMALL HETEROCYCLES/MACROCYCLIC CHEMISTRY

A.V. Bogatsky Physico-Chemical Institute, Odessa, Ukraine, PhD Thesis “Synthesis, structure and properties

of 2-aminobenzophenones oximes and their derivatives”, 2006 with Prof. Sergey Andronati

Anti-aggregation activity data for oximes

(ACSA = acetylsalicylic acid)

General approach to the synthesis of 16-membered

azomacrocycles An alternative route A

An alternative route B

Synthesis of 18-membered azamacrocycles

CCDC 713397

Attempted synthesis of 20-membered azamacrocycles