Intern
THE NOWAK-KRÓL GROUP: BORON-CONTAINING FUNCTIONAL MATERIALS

PUBLICATIONS

2024

51) Association of the benzoxazinoid pathway with boron homeostasis in maize
L. Chu, V. Shrestha, C. C. Schäfer, J. Niedens, G. W. Meyer, Z. Darnell, T. Kling, T. Dürr-Mayer, A. Abramov, M. Frey, H. Jessen, G. Schaaf, F. Hochholdinger, A. Nowak-Król, P. McSteen, R. Angelovici, M. S. Matthes*
Plant Physiol., accepted

50) Controllable 1,4-palladium aryl to aryl migration in fused systems – application to the synthesis of azaborole multihelicenes
F. Full, A. Artigas, K. Wiegand, D. Volland, K. Szkodzińska, Y. Coquerel, A. Nowak-Król*
J. Am. Chem. Soc., accepted
DOI: 10.1021/jacs.4c12562

49) Boron-containing helicenes as new generation of chiral materials: opportunities and challenges of leaving the flatland
A. Nowak-Król*, P. T. Geppert, K. R. Naveen
Chem. Sci. 202415, 7408-7440.
 DOI: 10.1039/d4sc01083c.
invited Perspective article

48) Dual nature of thiophene harnessed in the design of near-infrared emitters via antiaromaticity relief
A. Nowak-Król*
Angew. Chem. Int. Ed. 2024, 63, e202317060.
DOI: 10.1002/anie.202317060

2023

47) Site-specific PEGylation of recombinant tissue-type plasminogen activator
K. Meiners, P. Hamm, M. Gutmann, J. Niedens, A. Nowak-Król, S. Pané, T. Lühmann*
Eur. J. Pharm. Biopharm. 2023, 192, 79-87.
DOI: 10.1016/j.ejpb.2023.09.017

46) Impact of truncation on optoelectronic properties of azaborole helicenes
J. Full, M. J. Wildervanck, C. Dillmann, S. P. Panchal, D. Volland, F. Full, K. Meerholz, A. Nowak-Król*
Chem. Eur. J. 2023, e202302808.
DOI: 10.1002/chem.202302808

45) Synthesis of a blue-emissive azaborathia[9]helicene by silicon-boron exchange from unusual atropisomeric teraryls
D. Volland, J. Niedens, P. T. Geppert, M. J. Wildervanck, F. Full, A. Nowak-Król*
Angew. Chem. Int. Ed. 2023, e202304291.
DOI: 10.1002/anie.202304291
Part of the Special Collecton "Rethinking Chemistry"

44) Amber light control of peptide secondary structure by a perfluoroaromatic azobenzene photoswitch
E. Cataldi, M. Raschig M. Gutmann, P. T. Geppert, M. Ruopp, M. Schock, H. Gerwe, R. Bertermann, L. Meinel, M. Finze, A. Nowak-Król, M. Decker, T. Lühmann*
ChemBioChem, 2023, 24, e202200570.
DOI: 10.1002/cbic.202200570.

2022

43) Electrophilic C–H Borylation of Aza[5]helicenes Leading to Bowl-Shaped Quasi-[7]Circulenes with Switchable Dynamics
X. Zhang*, F. Rauch, J. Niedens, R. B. da Silva, A. Friedrich, A. Nowak-Król*, Simon J. Garden*, T. B. Marder*
J. Am. Chem. Soc. 2022, 144,  22316–22324.
DOI: 10.1021/jacs.2c10865
highlighted in ChemistryViews
highlighted in Synfacts:
N→B-Bridged Quasi-[7]circulenes
D. Zhao, X. Bai
Synfacts 2023, 19, 0243.
DOI: 10.1055/s-0042-1753326

42) 55th Bürgenstock Conference under the banner of sustainability
A. Nowak-Król*, P. Dydio*
Angew. Chem. Int. Ed. 2022, 61, e202214722.
DOI: 10.1002/anie.202214722
Angew. Chem. 2022, 134, e202214722.
DOI: 10.1002/ange.202214722
Meeting Report

41) Synthesis and strong solvatochromism of push-pull thienylthiazole boron complexes
M. J. Wildervanck, R. Hecht, A. Nowak-Król*
Molecules 2022, 27, 5510.
DOI: 10.3390/molecules27175510.
Special Collection ‘New Boron Chemistry: Current Advances and Future Prospects’, invited

40) Synthesis of enantioenriched azaborole helicenes by chirality transfer from axially chiral biaryls
F. Full, M. J. Wildervanck, D. Volland, A. Nowak-Król*
Synlett 202334, 477–482.
DOI: 10.1055/a-1914-1799.
SYNLETT Special Edition ‘Thieme Chemistry Journals Awardees 2022’

39) Enhanced Optical Properties of Azaborole Helicenes by Lateral and Helical Extension
F. Full, Q. Wölflick, K. Radacki, H. Braunschweig, A. Nowak-Król*
Chem. Eur. J. 2022, e202202280. (Hot Paper)
DOI: 10.1002/chem.202202280.
highlighted in Synfacts:
Azaborole Helicenes with Double Helical Axes
D. Zhao, X. Bai
Synfacts 2023, 19, 0143.
DOI: 10.1055/s-0042-1751818

38) Enhanced N-directed electrophilic C-H borylation generates BN- [5]- and [6]helicenes with improved photophysical properties
K. Yuan, D. Volland, S. Kirschner, M. Uzelac, G. S. Nichol, A. Nowak-Król*, M. J. Ingleson*
Chem. Sci. 202213, 1136–1145.
DOI: 10.1039/D1SC06513K
Part of the Special Collection on "Emerging Frontiers in Aromaticity"

2021

37) Modular synthesis of organoboron helically chiral compounds: cutouts from extended helices
J. Full, S. P. Panchal, J. Gӧtz, A.-M. Krause, A. Nowak-Król*
Angew. Chem. Int. Ed. 2021, 60, 4350–4357. (Hot Paper)
DOI: 10.1002/anie.202014138
Angew. Chem. 2021, 133, 4396–4403
DOI: 10.1002/ange.202014138
highlighted in ChemistryViews

2020

36) Access to corrole-appended persubstituted benzofurans by a multicomponent reaction: the dual role of p-chloranil
A. Nowak-Król*, B. Koszarna, M. Krzeszewski, T. D. Lohrey, J. Arnold*, D. T. Gryko*
Org. Lett. 2020, 22, 8139–8143.
DOI: 10.1021/acs.orglett.0c03133

2019

35) Ultrafast coherent exciton dynamics in size-controlled perylene bisimide aggregates
S. Kang, C. Kaufmann, Y. Hong, W. Kim, A. Nowak-Król, F. Würthner, D. Kim
Struct. Dyn. 2019, 6, 064501.
DOI: 10.1063/1.5124148

34) Tetrahydroxy-perylene bisimide embedded in a zinc oxide thin film as an electron-transporting layer 
for high-performance non-fullerene organic solar cells
X. Wen,# A. Nowak-Król,# O. Nagler, F. Kraus, N. Zhu, N. Zheng, M. Müller, D. Schmidt, Z. Xie, F. Würthner
Angew. Chem. Int. Ed. 2019, 58, 13051-13055.      
DOI: 10.1002/anie.201907467
Angew. Chem. 2019, 131, 13185-13189 
 DOI:10.1002/ange.201907467
# equal contribution
Press release


33) Low-melting porphyrins and their photophysical properties
A. Nowak-Król, D. T. Gryko
in Functional Organic Liquids; Ed. T. Nakanishi; Wiley-VCH, 2019
10.1002/9783527804948.ch2

 

 

32) Solvent-modulated charge-transfer resonance enhancement in the excimer state of a bay-substituted perylene bisimide 
cyclophane
W. Kim, A. Nowak-Król, Y. Hong, F. Schlosser, F. Würthner, D. Kim
J. Phys. Chem. Lett. 2019, 10, 1919–1927.
DOI: 10.1021/acs.jpclett.9b00357

 

 

31) Progress in the synthesis of perylene bisimide dyes
A. Nowak-Król, F. Würthner
Org. Chem. Front. 2019, 6, 1272-1318 (review).
DOI: 10.1039/C8QO01368C

 

2018

30) Naphthalene and perylene diimides – better alternatives to fullerenes for organic electronics?
A. Nowak-Król, K. Shoyama, M. Stolte, F. Würthner
Chem. Commun. 2018, 54, 13763-13772 (review).
DOI: 10.1039/C8CC07640E

 

 

29) Ultrafast exciton delocalization, localization, and excimer formation dynamics in a highly defined 
perylene bisimide quadruple π‑stack
C. Kaufmann, W. Kim, A. Nowak-Król, Y. Hong, D. Kim, F. Würthner
J. Am. Chem. Soc. 2018, 140, 4253-4258.
DOI: 10.1021/jacs.7b11571

 

2017

28) n-Channel organic semiconductors derived from air-stable four-coordinate boron complexes of substituted thienylthiazoles
R. Hecht, J. Kade, D. Schmidt, A. Nowak-Król*
Chem. Eur. J. 2017, 23, 11620-11628 (Hot Paper).
DOI: 10.1002/chem.201701922

 

 

27) A crystalline π-stack containing five stereoisomers: insights into conformational isomorphism, chirality inversion, and disorder
A. Nowak-Król, M. I. S. Röhr, D. Schmidt, F. Würthner
Angew. Chem. Int. Ed. 2017, 56, 11774-11778.
DOI: 10.1002/anie.201705445

Angew. Chem. 2017, 129, 11936-11940.
DOI: 10.1002/ange.201705445

 

2016

26) Direct observation of excimer-mediated intramolecular electron transfer in a cofacially-stacked perylene bisimide pair
J. Sung, A. Nowak-Król, F. Schlosser, B. Fimmel, W. Kim, D. Kim, F. Würthner
J. Am. Chem. Soc. 2016, 138, 9029-9032.
DOI: 10.1021/jacs.6b04591

25) Stable, low-melting trans-A2B-corroles
A. Nowak-Król, E. Fourie, C. C. Joubert, D. Gryko, D. T. Gryko, J. C. Swarts
J. Porphyrins Phthalocyanines 2016, 20, 1244-1255.
DOI: 10.1142/S1088424616500942

24) Modulation of band gap and p- versus n-semiconductor character of ADA dyes by core and acceptor group variation
A. Nowak-Król, R. Wagener, F. Kraus, A. Mishra, P. Bäuerle, F. Würthner
Org. Chem. Front. 2016, 3, 545-555.
DOI: 10.1039/C6QO00046K

23) Tetramethoxy-bay-substituted perylene bisimides by copper-mediated cross-coupling
P. Leowanawat, A. Nowak-Król, F. Würthner
Org. Chem. Front. 2016, 3, 537-544 (front cover).
DOI: 10.1039/C6QO00047A

2015

22) Photoinduced electron transfer (PET) versus excimer formation in supramolecular p/n-heterojunctions of perylene bisimide dyes and implications for organic photovoltaics
A. Nowak-Król, B. Fimmel, M. Son, D. Kim, F. Würthner
Faraday Discuss. 2015, 185, 507-527.
DOI: 10.1039/C5FD00052A

21) Liquid-crystalline properties of trans-A2B2-porphyrins with extended π-electron systems
M. Salamończyk, D. Pociecha, A. Nowak-Król, D. Koszelewski, D. T. Gryko, E. Górecka
Chem.Eur.J. 2015, 21 ,7384–7388.
DOI: 10.1002/chem.201500296

20) An efficient synthesis of porphyrins with different meso substituents that avoids scrambling in aqueous media
A. Nowak-Król, R. Plamont, G. Canard, J. A. Edzang, D. T. Gryko, T. S. Balaban
Chem. Eur. J. 2015, 21, 1488-1498 (inside cover).
DOI: 10.1002/chem.201403677

19) The 1H, 13C, 15N, and 19F NMR chemical shifts assignments in 5,10,15-tris(penta-fluorophenyl)tetra-15N corrole at 191 K
W. Bocian, P. Paluch, A. Nowak-Król, D. T. Gryko, M. Potrzebowski, J. Śniechowska, J. Sitkowski, E. Bednarek, L. Kozerski
Magn. Res. Chem. 2015, 53, 167-171.
DOI: 10.1002/mrc.4145

2014

18) Soluble meso-tetrakis(arylethynyl)porphyrins - synthesis and optical properties
A. Nowak-Król, Ł. G. Łukasiewicz, J. E. Haley, M. Drobizhev, A. Rebane, T. M. Cooper, D. T. Gryko
J. Porphyrins Phthalocyanines 2014, 18, 998-1013.
DOI: 10.1142/S1088424614500904

17) Two-photon absorption in butadiyne-linked porphyrin dimers: torsional and substituent effects
J. D. Wilkinson, G. Wicks, A. Nowak-Król, Ł. G. Łukasiewicz, C. J. Wilson, M. Drobizhev, A. Rebane, D. T. Gryko, H. L. Anderson
J. Mat. Chem. C 2014, 2, 6802-6809.
DOI: 10.1039/C4TC01120A

16) Insights into the tautomerism in meso-substituted corroles: a variable-temperature 1H, 13C, 15N, and 19F NMR spectroscopy study
S. Szymański, P. Paluch, D. T. Gryko, A. Nowak-Król, W. Bocian, J. Sitkowski, B. Koszarna, J. Śniechowska, M. J. Potrzebowski, L. Kozerski
Chem. Eur. J. 2014, 20, 1720-1730.
DOI: 10.1002/chem.201303406

2013

15) Oxidative aromatic coupling of meso-arylamino-porphyrins
A. Nowak-Król, D. T. Gryko
Org. Lett2013, 15, 5618-5621.
DOI: 10.1021/ol4022035

14) Study of intermolecular interactions in the corrole matrix by solid-state NMR under 100 kHz MAS and theoretical calculations
T. Kobayashi, K. Mao, P. Paluch, A. Nowak-Król, J. Sniechowska, Y. Nishiyama, D. T. Gryko, M. J. Potrzebowski, M. Pruski
Angew. Chem. Int. Ed. 2013, 52, 14108-14111.
DOI: 10.1002/anie.201305475
Angew. Chem. 2013,125, 14358-14361.
DOI: 10.1002/ange.201305475

13) All-optical corrole-based oxygen sensor
N. Czechowski, A. Nowak-Król, D. T. Gryko, S. Maćkowski
Phys. Scr. 2013, T157, 014009.
DOI: 10.1088/0031-8949/2013/T157/014009

12) Strong two-photon absorption enhancement in a unique bis-porphyrin bearing a diketopyrrolopyrrole unit
A. Nowak-Król, M. Grzybowski, J. Romiszewski, M. Drobizhev, G. Wicks, M. Chotkowski, A. Rebane, E. Górecka, D. T. Gryko
Chem. Commun. 2013, 49, 8368-8370.
10.1039/C3CC44728F

11) Synthesis and linear and nonlinear optical properties of low-melting π-extended porphyrins
D. Koszelewski, A. Nowak-Król, M. Drobizhev, C. J. Wilson, J. E. Haley, T. M. Cooper, J. Romiszewski, E. Górecka, H. L. Anderson, A. Rebane, D. T. Gryko
J. Mater. Chem. C 2013, 1, 2044-2053.
DOI: 10.1039/C3TC00594A

2012

10) Fluorescence microscopy of corrole-single silver nanowire hybrid nanostructures
N. Czechowski, M. Olejnik, A. Nowak-Król, D. Piątkowski, W. Heiss, D.T. Gryko, S. Mackowski
Acta Phys. Pol. A 2012, 122, 333-336.
DOI: 10.12693/APhysPolA.122.333

9) Amplified two-photon absorption in trans-A2B2-porphyrins bearing nitrophenylethynyl substituents
A. Nowak-Król, C. J. Wilson, M. Drobizhev, D. V. Kondratuk, A. Rebane, H. L. Anderson, D. T. Gryko
ChemPhysChem 2012, 13, 3966-3972 (Editor’s selection).
DOI: 10.1002/cphc.201200507

8) Selective cycloaddition of tetracyanoethene (TCNE) and 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) to afford meso-substituted phenylethynyl porphyrin
D. Koszelewski, A. Nowak-Król, D. T. Gryko
Chem. Asian J. 2012, 7, 1887-1894.
DOI: 10.1002/asia.201200179

2011

7) Synthesis of trans-A2B2-porphyrins bearing phenylethynyl substituents
A. Nowak-Król, B. Koszarna, S. Y. Yoo, J. Chromiński, M. K. Węcławski, C.-H. Lee, D. T. Gryko
J. Org. Chem2011, 76, 2627-2634.
DOI: 10.1021/jo1025578

2010

6) Mass spectrometry studies on meso-substituted corroles and their photochemical decomposition products
P. Świder, A. Nowak-Król, R. Voloshchuk, J. P. Lewtak, D. T. Gryko, W. Danikiewicz
J. Mass Spectrom. 2010, 45, 1443-1451.
DOI: 10.1002/jms.1860

5) meso-Alkylidene (m-benzi)pentaphyrin: a modified pentaphyrin bearing exocyclic double bonds at meso-positions
S.-D. Jeong, A. Nowak-Król, Y. Kim, S.-J. Kim, D. T. Gryko, C.-H. Lee
Chem. Commun. 2010, 8737-8739.
DOI: 10.1039/C0CC03263H

4) Synthesis and adrenolytic activity of new propanolamines
G. Groszek, A. Bajek, A. Bis, A. Nowak-Król, M. Bednarski, A. Siwek, B. Filipek
Molecules 2010, 15, 3887-3904.
DOI: 10.3390/molecules15063887

3) Meso-substituted liquid porphyrins
A. Nowak-Król, D. Gryko, D. T. Gryko
Chem. Asian J. 2010, 5, 904-909 (cover article).
DOI: 10.1002/asia.200900693

2009

2) Synthesis and adrenolytic activity of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxy-phenoxy)ethylamino)propan-2-ol analogs and its enantiomers. Part 2
G. Groszek, A. Nowak-Król, T. Wdowik, D. Świerczyński, M. Bednarski, M. Otto, M. Walczak, B. Filipek
Eur. J. Med. Chem. 2009, 44, 5103-5111.
DOI: 10.1016/j.ejmech.2009.07.012

2008

1) Straightforward transformation of pentafluorobenzaldehyde into 4-aryloxy-2,3,5,6-tetrafluorobenzaldehydes
D. T. Gryko, D. Wyrostek, A. Nowak-Król, K. Abramczyk, M. K. Rogacki
Synthesis­­ 2008, 4028-4032.
DOI: 10.1055/s-0028-1083246​​​​​​​

PATENTS

1) Nowe blokery optyczne oparte na bis-porfirynach o rozszerzonym chromoforze (New blockers based on bis-porphyrins with extended chromophores)
D. T. Gryko, A. Nowak-Król
Polish granted patent PL 223427 B1, 2016.