Supramolekulaarse keemia uurimisrühm
TalTech prioriteetne teadussuund
Klassifikaator (Frascati)
Uurimisrühma juht
Uurimisrühma liige
Doktorant
Võtmesõna
supramolekulaarsed retseptorid
roheline keemia
kukurbituriilid
kemosensorid
kiraalsus
orgaaniliste ühendite analüüs
monokristall röntgen difraktsioonanalüüs
spektroskoopia
UV-vis
FS
CD
VCD
Ülevaade
Supramolekulaarse keemia uurimisrühm tegeleb uute käeliste uureapõhiste molekulaarsete mahutite arendamisega. Tegeleme efektiivsete ja keskkonnasõbralike sünteesimeetodite välja töötamisega, kasutades muuhulgas mehhanokeemiat. Uurime molekulide ja supramolekulaarsete kompleksite struktuure ning molekulidevaheli vastasmõjusid. Keskendume kukurbituriilide perekonda kuuluvatele makrotsüklitele – hemikukurbituriilidele, ning nende kompleksidele. Eriti huvitume heade optiliste omadustega porpfüriinide kompleksitest ning nende rakendamisest supramolekulaarsetes süsteemides. Uurime kiraalse induktsiooni teket ning supramolekulaarsete komplesite spektroskoopilisi iseärasusi. Nii saame valmistada adaptiivseid sensoreid ning välisstiimulitele reageerivaid ise-organiseeruvaid molekulide süsteeme. Uute molekulaarsete mahutite disaini abil on võimalik välja töötada uusi rakendusi nii materjali- ja keskkonnateaduses, kui ka toidu-, farmaatsia- ning põllumajandustööstusele. Uurimisrühm panustab uute tehnoloogiate välja töötamisse üleeuroopalises teadlaste ja ettevõtjate konsortsiumites: https://www.project-initio.eu/ ja COST MechSustInd.
Tähtsamad tulemused
Olulisemateks tulemusteks 2022 aastal on kiraalsete hemikukurbituriilide homoloogide eristuvad seostumisomadused bisporfüriinidega komplekside tekkel (Molecules 2022) ja keskkonnasõbraliku mehhanokeemilise asendatud amiinide sünteesi väljatöötamine (ChemSusChem 2022).
Seotud projektid
Seotud struktuuriüksus
Teadusgrupiga seotud publikatsioonid
- Dalidovich, T., Nallaparaju, J. V., Shalima, T., Aav, R., Kananovich, D. G. Mechanochemical nucleophilic substitution of alcohols via isouronium intermediates // ChemSusChem (2022) vol. 15, 3, art. e202102286.
https://doi.org/10.1002/cssc.202102286 - Šakarašvili, M., Ustrnul, L., Suut, E., Nallaparaju, J.V., Mishra, K.A., Konrad, N., Adamson, J., Borovkov, V., Aav, R. Self-assembly of chiral cyclohexanohemicucurbit[n]urils with bis(Zn porphyrin): size, shape, and time-dependent binding // Molecules (2022) vol. 27, 3, art. 937, 13 p. : ill.
https://doi.org/10.3390/molecules27030937 - Shalima, T., Mishra, K.A., Kaabel, S., Ustrnul, L., Bartkova, S., Tõnsuaadu, K., Heinmaa, I., Aav, R. Cyclohexanohemicucurbit[8]uril inclusion complexes with heterocycles and selective extraction of sulfur compounds from water // Frontiers in chemistry (2021) Vol. 9, art. 786746, 8 p. : ill.
https://doi.org/10.3389/fchem.2021.786746 - Konrad, N., Horetski, M., Sihtmäe, M., Osadchuk, I., Senge, M. O., Borovkov, V., Aav, R., Kananovich, D. et al. Thiourea organocatalysts as emerging chiral pollutants : en route to porphyrin-based (chir)optical sensing // Chemosensors (2021) vol. 9, 10, art. 278.
https://doi.org/10.3390/chemosensors9100278 - Salvatore, L., Gallo, N., Gallo, N., Borovkov, V. et al. An insight on type I collagen from horse tendon for the manufacture of implantable devices // International journal of biological macromolecules (2020) Vol. 154, 1, p. 291-306.
https://doi.org/10.1016/j.ijbiomac.2020.03.082 - Sharma, M., Hussain, S., Shalima, T., Aav, R., Bhat, R. Valorization of seabuckthorn pomace to obtain bioactive carotenoids: An innovative approach of using green extraction techniques (ultrasonic and microwave-assisted extractions) synergized with green solvents (edible oils) // Industrial Crops and Products (2022) vol. 175, art. 114257.
https://doi.org/10.1016/j.indcrop.2021.114257 - Dalidovich, T., Mishra, K.A., Shalima, T., Kudrjašova, M., Kananovich, D. G., Aav, R. Mechanochemical synthesis of amides with uronium-based coupling reagents : a method for hexa-amidation of biotin[6]uril // ACS sustainable chemistry & engineering (2020) vol. 8, 41, p. 15703−15715 : ill.
https://doi.org/10.1021/acssuschemeng.0c05558 - Kanagaraj, K., Xiao, C., Rao, M., Fan, C., Borovkov, V. et al. A quinoline-appended cyclodextrin derivative as a highly selective receptor and colorimetric probe for nucleotides // iScience (2020) vol. 23, 3, art. 100927, 67 p. : ill.
https://doi.org/10.1016/j.isci.2020.100927 - Yin, Z., Guo, J., Zhang, R., Hu, X., Borovkov, V. Direct asymmetric three-component Mannich reaction catalyzed by chiral counteranion-assisted silver // The journal of organic chemistry (2020) vol. 85, 16, p. 10369−10377 : ill.
https://doi.org/10.1021/acs.joc.0c00031 - Laanesoo, S., Bonjour, O., Parve, J., Parve, O., Matt, L., Vares, L., Jannasch, P. Poly(alkanoyl isosorbide methacrylate)s : from amorphous to semicrystalline and liquid crystalline biobased materials // Biomacromolecules (2021) vol. 22, 2, p. 640-648.
https://doi.org/10.1021/acs.biomac.0c01474 - Khose, V.N., Hasan, M., Khot, S.C., Mobin, S.M., Borovkov, V. et al. Directional Approach to Enantiomerically Enriched Functionalized [7]Oxa-helicenoids and Groove-Based Selective Cyanide Sensing // Journal of organic chemistry (2019) vol. 85, 4, p. 1847−1860 : ill.
https://doi.org/10.1021/acs.joc.9b02100 - Kananovich, D., Elek, G. Z., Lopp, M., Borovkov, V. Aerobic oxidations in asymmetric synthesis : catalytic strategies and recent developments // Frontiers in chemistry (2021) vol. 9, art. 614944.
https://doi.org/10.3389/fchem.2021.614944 - Hu, X., Guo, J., Wang, C., Zhang, R., Borovkov, V. Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups // Beilstein journal of organic chemistry (2020) vol. 16, p. 1875−1880.
https://doi.org/10.3762/bjoc.16.155 - Trubitsõn, D., Martõnova, J., Kudrjašova, M., Erkman, K., Järving, I., Kanger T. Enantioselective organocatalytic Michael addition to unsaturated indolyl ketones // Organic letters (2021) vol. 23, 5, p. 1820-1824.
https://doi.org/10.1021/acs.orglett.1c00222 - Konik, Y.A., Kananovich, D.G. Asymmetric synthesis with titanacyclopropane reagents : From early results to the recent achievements // Tetrahedron letters (2020) vol. 61, 26, art. 152036, 12 p. : ill.
https://doi.org/10.1016/j.tetlet.2020.152036 - Mishra, K.A., Adamson, J., Öeren, M., Kaabel, S., Fomitšenko, M., Aav, R. Dynamic chiral cyclohexanohemicucurbit[12]uril // Chemical communications (2020) vol. 56, 93, p. 14645−14648.
https://doi.org/10.1039/D0CC06817A - Ivanova, L., Rausalu, K., Ošeka, M., Kananovich, D. G., Žusinaite, E., Tammiku-Taul, J., Lopp, M., Merits, A., Karelson, M. Novel analogues of the Chikungunya virus protease inhibitor: molecular design, synthesis, and biological evaluation // ACS omega (2021) vol. 6, 16, p. 10884–10896.
https://doi.org/10.1021/acsomega.1c00625 - Mariichak, O., Kaabel, S., Karpichev, Y. et al. Crystal structure and magnetic properties of Peacock- Weakley type polyoxometalates Na9[Ln(W5O18)2] (Ln = Tm, Yb): Rare example of Tm(III) SMM // Magnetochemistry (2020) vol. 6(4), 53, 14 p. : ill.
https://doi.org/10.3390/magnetochemistry6040053 - Ward, J. S., Martõnova, J., Wilson, L. M. E., Kramer, E., Aav, R., Rissanen, K. Carbonyl hypoiodites from pivalic and trimesic acid and their silver(i) intermediates // Dalton Transactions (2022) vol. 51, 38, p. 14646-14653.
https://doi.org/10.1039/D2DT01988D - Pandya, S. J., Kapitanov, I. V., Borovkov, V., Ghosh, K. K., Karpichev, Y. et al. Mixed oxime-functionalized IL/16-s-16 Gemini surfactants system: physicochemical study and structural transitions in the presence of promethazine as a potential chiral pollutant // Chemosensors (2022) vol. 10, 2, art. 46.
https://doi.org/10.3390/chemosensors10020046 - Masiuk, U.S., Mineyeva, I.V., Kananovich, D.G. Highly diastereoselective chelation-controlled 1,3-anti-allylation of (S)-3-(Methoxymethyl)hexanal enabled by hydrate of scandium triflate // Symmetry (2021) vol. 13, 3, art. 470, 17 p.
https://doi.org/10.3390/sym13030470 - Osadchuk, I., Konrad, N., Truong, K.-N., Aav, R., Kananovich, D., Borovkov, V. et al. Supramolecular Chirogenesis in bis-porphyrin: crystallographic structure and CD spectra for a complex with a chiral guanidine derivative // Symmetry (2021) vol. 13, 275, 14 p. : ill.
https://doi.org/10.3390/sym13020275 - Osadchuk, I., Borovkov, V., Aav, R., Clot, E. Benchmarking computational methods and influence of guest conformation on chirogenesis in zinc porphyrin complexes // Physical chemistry chemical physics (2020) vol. 22, 19, p. 11025−11037.
https://doi.org/10.1039/D0CP00965B - Konrad, N., Meniailava, D., Osadchuk, I., Adamson, J., Hasan, M., Aav, R., Borovkov, V., Kananovich, D. et al. Supramolecular chirogenesis in zinc porphyrins: complexation with enantiopure thiourea derivatives, binding studies and chirality transfer mechanism // Journal of porphyrins and phthalocyanines (2020)
https://doi.org/10.1142/S108842461950192X - Peterson, A., Ludvig, M-L., Martõnova, J., Kaabel, S., Fomitšenko, M., Aav, R. et al. New oxacalix[4]arene carboxylate detects viologen in protic media // Supramolecular chemistry (2020) vol. 32, 5, p. 313–319 : ill.
https://doi.org/10.1080/10610278.2019.1659269 - Parve, J., Kudryašova, M., Shalima, T., Villo, L., Liblikas, I., Reile, I., Pehk, T., Gathergood, N., Aav, R., Vares, L., Parve, O. Scalable lipase-catalyzed synthesis of (R)-4-(Acyloxy)pentanoic acids from racemic γ-valerolactone // ACS sustainable chemistry & engineering (2021) vol. 9, 4, p. 1494−1499.
https://doi.org/10.1021/acssuschemeng.0c07918 - Sun, Y., Aav, R., Borovkov, V. et al. Supramolecular chirogenesis in chemical and related sciences : editorial // Frontiers in chemistry (2021) vol. 9, art. 679332.
https://doi.org/10.3389/fchem.2021.679332 - Hu, X., Yin, Z., Guo, J., Adamson, J., Fujiki, M., Borovkov, V. Stereospecific synthesis of cyclic sulfite esters with sulfur-centered chirality via diastereoselective strategy and intramolecular H-Bonding assistance // Journal of Organic Chemistry (2021) Vol. 86, 1, p. 379 - 387.
https://doi.org/10.1021/acs.joc.0c02147 - Ustrnul, L., Burankova, T., Öeren, M., Juhhimenko, K., Ilmarinen, J., Siilak, K., Mishra, K. A., Aav, R. Binding between cyclohexanohemicucurbit[n]urils and polar organic guests // Frontiers in chemistry (2021) Vol. 9, art. 701028.
https://doi.org/10.3389/fchem.2021.701028 - Kanagaraj, K., Yang, C., Borovkov, V. Chirogenesis in supramolecular systems // Fundamentals of supramolecular chirality. : World Scientific Publishing, 2021. p. 85-147.
https://doi.org/10.1142/9781800610255_0004 - Osadchuk, I., Aav, R., Borovkov, V., Clot, E. Chirogenesis in Zinc porphyrins : theoretical evaluation of electronic transitions, controlling structural factors and axial ligation // ChemPhysChem (2021) vol. 22, 17, p. 1817−1833 : ill.
https://doi.org/10.1002/cphc.202100345 - Prigorchenko, E., Ustrnul, L., Borovkov, V., Aav, R. Heterocomponent ternary supramolecular complexes of porphyrins : a review // Porphyrin Science by Women. Volume 3: Materials, Sensors, Energy and Catalysis. : World Scientific Publishing, 2021. p. 816-833.
https://doi.org/10.1142/9789811223556_0071 - Borovkov, V. (eds.) Chiral auxiliaries and chirogenesis ii // Symmetry (2021) Vol. 13, 7, art. 1157.
https://doi.org/10.3390/sym13071157 - Zubrytski, D. M., Elek, G. Z., Lopp, M., Kananovich, D. G. Generation of mixed anhydrides via oxidative fragmentation of tertiary cyclopropanols with phenyliodine(III) dicarboxylates // Molecules (2020) vol. 26, 1, art. 140.
https://doi.org/10.3390/molecules26010140 - Hu, X., Li, K., Guo, J., Wang, C., Ma, L., Borovkov, V. Highly chemo- and regioselective synthesis and subsequent directional catalyst-free transformation of enantiopure bioxirane derivatives // Tetrahedron (2022) vol. 113, art. 132763.
https://doi.org/10.1016/j.tet.2022.132763 - Chen, Z., Deng, D.-D., Aav, R., Borovkov, V., Sun, Y. Editorial : Stimuli-responsive emissive organic and metal-organic compounds // Frontiers in chemistry (2022) vol. 10, art. 946617.
https://doi.org/10.3389/fchem.2022.946617 - Borovkov, V., Aav, R. (eds.). Chirogenesis in Chemical Science. 1. Singapore : World Scientific Publishing, 2023. 520 p.
https://doi.org/10.1142/12915 - Kananovich, D. G., Lopp, M. Chirogenesis in asymmetric synthesis and catalysis // Chirogenesis in Chemical Science. Singapore : World Scientific Publishing, 2023. p. 169-240.
https://doi.org/10.1142/9789811259227_0004 - Xiao, T., James, T. D., Borovkov, V., Castellano, R. K., Deng, C. Suprastars of chemistry : editorial // Frontiers in Chemistry (2022) vol. 10, art. 932508.
https://doi.org/10.3389/fchem.2022.932508 - Ustrnul, L., Borovkov, V., Aav, R. Chirogenesis in supramolecular systems // Chirogenesis in Chemical Science. Singapore : World Scientific Publishing, 2023. p. 69-123.
https://doi.org/10.1142/9789811259227_0002 - Borovkov, V., Aav, R. Preface // Chirogenesis in Chemical Science. : World Scientific Publishing, 2023. p. vii-xi.
https://doi.org/10.1142/9789811259227_fmatter - Manera, M. G., Giancane, G., Borovkov, V. et al. Magnetoplasmonic waves/HOMO-LUMO free π-electron transitions coupling in organic macrocycles and their effect in sensing applications // Chemosensors (2021) vol. 9, 10, art. 272.
https://doi.org/10.3390/chemosensors9100272 - Norvaiša, K., O’Brien, J. E., Osadchuk, I., Twamley, B., Borovkov, V., Senge, M. O. Importance of molecular symmetry for enantiomeric excess recognition by NMR // Chemical communications (2022) vol. 58, 35, p. 5423-5426.
https://doi.org/10.1039/D2CC01319C - Du, R., Han, L., Zhou, Z., Borovkov, V. Efficient synthesis of novel quinolinone derivatives via catalyst-free multicomponent reaction // Letters in organic chemistry (2020) vol. 17, 5, p. 403−407.
http://doi.org/10.2174/1570178616666190828092728 - Hu, X., Yin, Zh., Guo, J., Borovkov, V., Shan, Z. An efficient method for long‐term configurational stabilization of chiral tricyclic dipeptide via heterocomplexation approach // ChemistrySelect (2019) vol. 4, 11, p. 3210-3213.
https://doi.org/10.1002/slct.201900099 - Yin, Zh., Xiong, Ch., Guo J., Hu, X., Shan, Z., Borovkov, V. Highly chemoselective solvent-free synthesis of 1,3,5-triaryl-1,5- diketones: crystallographic investigation and intramolecular weak bifurcated H bonds involving aliphatic C-H group // Synlett (2019) vol. 30, p. 2143−2147.
https://doi.org/10.1055/s-0039-1690224 - Maljutenko, K., Borovkov, V., Kananovich, D., Järving, I., Lopp, M. Aerobic cascade oxidation of substituted cyclopentane-1,2-diones using metalloporphyrin catalysts // Tetrahedron (2018) vol. 74, 6, p. 661−664 : ill.
https://doi.org/10.1016/j.tet.2017.12.009 - Murre, A., Erkman, K., Kaabel, S., Järving, I., Kanger, T. Diastereoselective [2,3]-sigmatropic rearrangement of N-allyl ammonium ylides // Synthesis (2019) vol. 51, 22, p. 4183–4197.
https://doi.org/10.1055/s-0039-1690185 - Silm, E., Kaabel, S., Järving, I., Kanger, T. Asymmetric organocatalytic Michael addition–cyclisation cascade of cyclopentane-1,2-dione with alkylidene malononitriles // Synthesis (2019) vol. 51, 22, p. 4198-4204.
https://doi.org/10.1055/s-0039-1690484 - Buccolieri, A., Manno, D., Serra, A., Santino, A., Hasan, M., Borovkov, V., Giancane, G. Highly sensitive conformational switching of ethane-bridged mono-zinc bis-porphyrin as an application tool for rapid monitoring of aqueous ammonia and acetone // Sensors and actuators B : chemical (2018) vol. 257, p. 685-691 : ill.
https://doi.org/10.1016/j.snb.2017.11.021 - Osawa T., Wakasugi M., Kizawa T., Borovkov V., Inoue Y. Enantio-differentiating hydrogenation of alkyl 3-oxobutanoates over tartaric acid-modified Ni catalyst: Enthalpy-entropy compensation effect as a tool for elucidating mechanistic features // Molecular catalysis (2018) vol. 449, p. 131-136 : ill.
https://doi.org/10.1016/j.mcat.2018.02.023 - Prigorchenko, E. Kaabel, S., Narva, T., Baškir, A., Fomitšenko, M., Adamson, J., Järving, I., Rissanen, K., Tamm, T., Aav, R. Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril // Chemical communications (2019) vol. 55, 63, p. 9307−9310 : ill.
https://doi.org/10.1039/C9CC04990H - Prigorchenko, E., Ustrnul, L., Borovkov, V., Aav, R. Heterocomponent ternary supramolecular complexes of porphyrins: a review // Journal of porphyrins and phthalocyanines (2019) vol. 23, 11-12, p. 1308-1325 : ill.
https://doi.org/10.1142/S108842461930026X - Buccolieri, A., Hasan, M., Bettini, S., Borovkov, V. et al. Ethane-bridged bisporphyrin conformational changes as an effective analytical tool for nonenzymatic detection of urea in the physiological range // Analytical chemistry (2018) vol. 90, 11, p. 6952-6958 : ill.
https://doi.org/10.1021/acs.analchem.8b01230 - Kimm, M., Ošeka, M., Kaabel, S., Metsala, A., Järving, I., Kanger, T. [2,3]-Wittig rearrangement as a formal asymmetric alkylation of α-branched ketones // Organic letters (2019) vol. 21, 13, p. 4976-4980.
https://doi.org/10.1021/acs.orglett.9b01495 - Trubitsõn, D., Žari, S., Kaabel, S., Kudrjashova, M., Kriis, K., Järving, I., Pehk, T., Kanger, T. Asymmetric organocatalytic cascade synthesis of tetrahydrofuranyl spirooxindoles // Synthesis (2018) vol. 50, 2, p. 314-322 : ill.
https://doi.org/10.1055/s-0036-1590918 - Gawade, P. M.; Khose, V. N.; Badani, P. M., Kaabel, S., Borovkov, V. et al. Benzyne-mediated nonconcerted pathway toward synthesis of sterically crowded [5]- and [7]oxahelicenoids, stereochemical and theoretical studies, and optical resolution of helicenoids // Journal of organic chemistry (2019) vol. 84, 2, p. 860-868 : ill.
https://doi.org/10.1021/acs.joc.8b02507 - Ermolovich, Y., Barysevich, M., Adamson, J., Rogova, O., Kaabel, S., Järving, I.,Gathergood, N., Kananovich, D. G. Site-selective and stereoselective C–H functionalization of N-Cyclopropylamides via a directed remote metalation strategy // Organic letters (2019) vol. 21, 4, p. 969-973 : ill.
https://doi.org/10.1021/acs.orglett.8b03955 - Khose V.N., John M.E., Pandey A.D., Borovkov V., Karnik A.V. Chiral heterocycle-based receptors for enantioselective recognition // Symmetry (2018) vol. 10, 2, 75 p : ill.
https://doi.org/10.3390/sym10020034 - Elek, G.Z., Koppel, K., Zubrytski, D., Konrad, N., Järving, I., Lopp, M., Kananovich, D. Divergent access to histone deacetylase inhibitory cyclopeptides via a late-stage cyclopropane ring Cleavage strategy. Short synthesis of Chlamydocin // Organic letters (2019) vol. 21, 20, p. 8473-8478 : ill.
https://doi.org/10.1021/acs.orglett.9b03305 - Adamson, J., Nazarski, R. B., Jarvet, J. Pehk, T., Aav, R. Shortfall of B3LYP in reproducing NMR JCH couplings in some isomeric epoxy structures with strong stereoelectronic effects : a benchmark study on DFT functionals // ChemPhysChem (2018) vol. 19, 5, p. 631-642 : ill.
https://doi.org/10.1002/cphc.201701125 - Kaabel, S., Aav, R. Templating effects in the dynamic chemistry of Cucurbiturils and Hemicucurbiturils // Israel journal of chemistry (2018) vol. 58, 3/4, p. 296−313 : ill.
https://doi.org/10.1002/ijch.201700106 - Aav, R., Mishra, K. The breaking of symmetry leads to chirality in cucurbituril-type hosts // Symmetry (2018) vol. 10, 4, 26 p. : ill.
https://doi.org/10.3390/sym10040098 - Ustrnul, L., Kaabel, S., Burankova, T., Martõnova, J., Konrad, N., Borovkov, V., Aav, R. et al. Supramolecular chirogenesis in zinc porphyrins by enantiopure hemicucurbit[n]urils (n = 6, 8) // Chemical communications (2019) vol. 55, 96, p. 14434-14437 : ill.
https://doi.org/10.1039/c9cc07150d - Bettini, S., Pagano, R., Borovkov, V., Giancane, G., Valli, L. The role of the central metal ion of ethane-bridged bis-porphyrins in histidine sensing // Journal of colloid and interface science (2019) vol. 533, p. 762-770 : ill.
https://doi.org/10.1016/j.jcis.2018.08.116 - Peterson, A., Kaasik, M., Metsala, A., Järving, I., Adamson, J., Kanger, T. Tunable chiral triazole-based halogen bond donors : assessment of donor strength in solution with nitrogen-containing acceptors // RSC advances (2019) vol. 9, 21, p. 11718–11721 : ill.
https://doi.org/10.1039/c9ra01692a - Kaasik, M., Kaabel, S., Kriis, K., Järving, I., Kanger, T. Synthesis of chiral triazole-based halogen bond donors // Synthesis (2019) vol. 51, 10, p. 2128-2135 : ill.
https://doi.org/10.1055/s-0037-1610864 - Mamardashvili, G., Maltceva, O., Lazovskiy, D., Khodov, I., Borovkov, V. et al. Medium viscosity effect on fluorescent properties of Sn(IV)-tetra(4-sulfonatophenyl)porphyrin complexes in buffer solutions // Journal of molecular liquids (2019) vol. 277, p. 1047-1053 : ill.
https://doi.org/10.1016/j.molliq.2018.12.118 - Kaabel, S., Stein, R. S., Fomitšenko, M., Järving, I., Frišcic, T, Aav, R. Size-control by anion templating in mechanochemical synthesis of hemicucurbiturils in the solid state // Angewandte Chemie international edition (2019) vol. 58, 19, p. 6230-6234 : ill.
https://doi.org/10.1002/anie.201813431 - Matt, L., Parve, J., Parve, O., Pehk, T., Liblikas, I., Vares, L., Jannasch, P. et al. Enzymatic synthesis and polymerization of isosorbide-based monomethacrylates for high-Tg plastics // ACS sustainable chemistry & engineering (2018) vol. 6, 12, p. 17382-17390.
https://doi.org/10.1021/acssuschemeng.8b05074 - Hasan, M., Borovkov, V. Helicene-based chiral auxiliaries and chirogenesis // Symmetry (2018) vol. 10, 1, 48 p. : ill.
https://doi.org/10.3390/sym10010010 - Kaasik, M., Metsala, A., Kaabel, S., Kriis, K., Järving, I., Kanger, T. Halo-1,2,3-triazolium salts as halogen bond donors for the activation of imines in dihydropyridinone synthesis // Journal of organic chemistry (2019) vol. 84, 7, p. 4294–4303 : ill.
https://doi.org/10.1021/acs.joc.9b00248