Publications

50

Garain, S.; Li, P.-L.; Shoyama, K.; Würthner, F. 2,3:6,7‒Naphthalene Bis(Dicarboximide) Cyclophane: A Photo‒functional Host for Ambient Delayed Fluorescence in Solution. Angew. Chem. Int. Ed. 2024, e202411102. https://doi.org/10.1002/anie.202411102.

49

Niyas, M. A.; Garain, S.; Shoyama, K.; Würthner, F. Room-Temperature Near-Infrared Phosphorescence from C₆₄ Nanographene Tetraimide by π-Stacking Complexation with Platinum Porphyrin. Angew. Chem. Int. Ed. 2024, e202406353. https://doi.org/10.1002/anie.202406353.

48

Mützel, C.; Shoyama, K.; Krause, A.-M.; Würthner, F. Synthesis of a Helical Boron-Doped PAH by Post-Functionalization of 3,9-Diboraperylene. Org. Chem. Front. 2024, 11 (10), 2747–2755. https://doi.org/10.1039/d4qo00421c.

47

Rühe, J.; Rajeevan, M.; Shoyama, K.; Swathi, R. S.; Würthner, F. A Terrylene Bisimide Based Universal Host for Aromatic Guests to Derive Contact Surface-Dependent Dispersion Energies. Angew. Chem. Int. Ed. 2024, 63 (17), e202318451. https://doi.org/10.1002/anie.202318451.

46

Herbert, B.; Walpuski, J.; Stolte, M.; Shoyama, K. Designing Organic π-Conjugated Molecules for Crystalline Solid Solutions: Adamantane-Substituted Naphthalenes. ChemPlusChem 2024, 89 (6), e202300761. https://doi.org/10.1002/cplu.202300761.

45

Schnitzlein, M.; Shoyama, K.; Würthner, F. A Highly Fluorescent Bora[6]Helicene Exhibiting Circularly Polarized Light Emission. Chem. Sci. 2024, 15 (8), 2984–2989. https://doi.org/10.1039/d3sc05171d.

44

Nagler, O.; Shoyama, K.; Anhalt, O.; Stolte, M.; Dubey, R. K.; Xie, Z.; Würthner, F. Boron-, Carbon-, and Silicon-Bridged 1,12-Dihydroxy-Perylene Bisimides with Tuned Structural and Optical Properties. Org. Chem. Front. 2023, 10 (22), 5685–5697. https://doi.org/10.1039/d3qo01389h.

43

Spengler, J.; Zhu, C.; Shoyama, K.; Würthner, F. π-Extended Benzo[1,2:4,5]di[7]annulene Bis(dicarboximide)s – a New Class of Non-Alternant Polycyclic Aromatic Dicarboximides. Chem. Sci. 2023, 14 (39), 10861–10866. https://doi.org/10.1039/d3sc04015a.

42

Mahlmeister, B.; Schembri, T.; Stepanenko, V.; Shoyama, K.; Stolte, M.; Würthner, F. Enantiopure J‑Aggregate of Quaterrylene Bisimides for Strong Chiroptical NIR-Response. J. Am. Chem. Soc. 2023, 145 (24), 13302–13311. https://doi.org/10.1021/jacs.3c03367.

41

Tian, X.; Shoyama, K.; Mahlmeister, B.; Brust, F.; Stolte, M.; Würthner, F. Naphthalimide-Annulated [n]Helicenes: Red Circularly Polarized Light Emitters. J. Am. Chem. Soc. 2023, 145 (17), 9886–9894. https://doi.org/10.1021/jacs.3c03441.

40

Kleine-Kleffmann, L.; Stepanenko, V.; Shoyama, K.; Wehner, M.; Würthner, F. Controlling the Supramolecular Polymerization of Squaraine Dyes by a Molecular Chaperone Analogue. J. Am. Chem. Soc. 2023, 145 (16), 9144–9151. https://doi.org/10.1021/jacs.3c01002.

39

Niyas, M. A.; Shoyama, K.; Würthner, F. C₆₄ Nanographene Tetraimide—A Receptor for Phthalocyanines with Subnanomolar Affinity. Angew. Chem. Int. Ed. 2023, 62 (25), e202302032. https://doi.org/10.1002/anie.202302032.

38

Weh, M.; Kroeger, A. A.; Shoyama, K.; Grüne, M.; Karton, A.; Würthner, F. π-π Catalysis Made Asymmetric—Enantiomerization Catalysis Mediated by the Chiral π-System of a Perylene Bisimide Cyclophane. Angew. Chem. Int. Ed. 2023, 62 (19), e202301301. https://doi.org/10.1002/anie.202301301.

37

Menekse, K.; Mahl, M.; Albert, J.; Niyas, M. A.; Shoyama, K.; Stolte, M.; Würthner, F. Supramolecularly Engineered Bulk-Heterojunction Solar Cells with Self-Assembled Non-Fullerene Nanographene Tetraimide Acceptors. Sol RRL 2023, 7 (2), 2200895. https://doi.org/10.1002/solr.202200895.

36

Labella, J.^‡; Shoyama, K.^‡; Guzmán, D.; Schembri, T.; Stolte, M.; Torres, T.; Würthner, F. Naphthalimide-Fused Subphthalocyanines: Electron-Deficient Materials Prepared by Cascade Annulation. ACS Mater. Lett. 2023, 5 (2), 543–548. https://doi.org/10.1021/acsmaterialslett.2c01132. ^‡ Contributed equally

35

Weh, M.; Shoyama, K.; Würthner, F. Preferential Molecular Recognition of Heterochiral Guests within a Cyclophane Receptor. Nat. Commun. 2023, 14 (1), 243. https://doi.org/10.1038/s41467-023-35851-3.

34

Brust, F.; Nagler, O.; Shoyama, K.; Stolte, M.; Würthner, F. Organic Light-Emitting Diodes Based on Silandiol-Bay-Bridged Perylene Bisimides. Adv. Opt. Mater. 2023, 11 (5), 2202676. https://doi.org/10.1002/adom.202202676.

33

Noll, N.; Groß, T.; Shoyama, K.; Beuerle, F.; Würthner, F. Folding-Induced Promotion of Proton-Coupled Electron Transfers via Proximal Base for Light-Driven Water Oxidation. Angew. Chem. Int. Ed. 2023, 62 (7), e202217745. https://doi.org/10.1002/anie.202217745.

32

Tian, X.; Shoyama, K.; Würthner, F. Nitrogen-Doped Polycyclic Aromatic Hydrocarbons by a One-Pot Suzuki Coupling/Intramolecular S_NAr Reaction. Chem. Sci. 2022, 14 (2), 284–290. https://doi.org/10.1039/d2sc05409d.

31

Nagler, O.; Krause, A.-M.; Shoyama, K.; Stolte, M.; Dubey, R. K.; Liu, L.; Xie, Z.; Würthner, F. Yellow Light-Emitting Highly Soluble Perylene Bisimide Dyes by Acetalization of Bay-Hydroxy Groups. Org. Lett. 2022, 24 (37), 6839–6844. https://doi.org/10.1021/acs.orglett.2c02764.

30

Zhu, C.^‡; Shoyama, K.^‡; Niyas, M. A.; Würthner, F. Supramolecular Substructure of C₆₀-Embedded Schwarzite. J. Am. Chem. Soc. 2022, 144 (36), 16282–16286. https://doi.org/10.1021/jacs.2c06933. ^‡ Contributed equally

29

Schnitzlein, M.; Zhu, C.; Shoyama, K.; Würthner, F. π-Extended Pleiadienes by [5+2] Annulation of 1-Boraphenalenes and ortho-Dihaloarenes. Chem. Eur. J. 2022, 28 (61), e202202053. https://doi.org/10.1002/chem.202202053.

28

Hong, Y.; Rudolf, M.; Kim, M.; Kim, J.; Schembri, T.; Krause, A.-M.; Shoyama, K.; Bialas, D.; Röhr, M. I. S.; Joo, T.; Kim, H.; Kim, D.; Würthner, F. Steering the Multiexciton Generation in Slip-Stacked Perylene Dye Array via Exciton Coupling. Nat. Commun. 2022, 13 (1), 4488. https://doi.org/10.1038/s41467-022-31958-1.

27

Mahlmeister, B.; Mahl, M.; Reichelt, H.; Shoyama, K.; Stolte, M.; Würthner, F. Helically Twisted Nanoribbons Based on Emissive Near-Infrared Responsive Quaterrylene Bisimides. J. Am. Chem. Soc. 2022. https://doi.org/10.1021/jacs.2c02947.

26

Pigulski, B.; Shoyama, K.; Sun, M.-J.; Würthner, F. Fluorescence Enhancement by Supramolecular Sequestration of a C₅₄-Nanographene Trisimide by Hexabenzocoronene. J. Am. Chem. Soc. 2022, 144 (13), 5718–5722. https://doi.org/10.1021/jacs.2c00142.

25

Bold, K.; Stolte, M.; Shoyama, K.; Krause, A.-M.; Schmiedel, A.; Holzapfel, M.; Lambert, C.; Würthner, F. Macrocyclic Donor−Acceptor Dyads Composed of Oligothiophene Half-Cycles and Perylene Bisimides. Chem. Eur. J. 2022. https://doi.org/10.1002/chem.202200355.

24

Mahl, M.; Niyas, M. A.; Shoyama, K.; Würthner, F. Multilayer Stacks of Polycyclic Aromatic Hydrocarbons. Nat. Chem. 2022, 14 (4), 457–462. https://doi.org/10.1038/s41557-021-00861-5.

23

Schnitzlein, M.; Mützel, C.; Shoyama, K.; Farrell, J. M.; Würthner, F. PAHs Containing Both Heptagon and Pentagon: Corannulene Extension by [5+2] Annulation. Eur. J. Org. Chem. 2022, 2022 (5). https://doi.org/10.1002/ejoc.202101273.

22

Mützel, C.; Farrell, J. M.; Shoyama, K.; Würthner, F. 12b,24b-Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low-LUMO Boron-Doped Polycyclic Aromatic Hydrocarbon. Angew. Chem. Int. Ed. 2022, 61 (8), e202115746. https://doi.org/10.1002/anie.202115746.

21

Bold, K.; Stolte, M.; Shoyama, K.; Holzapfel, M.; Schmiedel, A.; Lambert, C.; Würthner, F. Macrocyclic Donor–Acceptor Dyads Composed of a Perylene Bisimide Dye Surrounded by Oligothiophene Bridges. Angew. Chem. Int. Ed. 2022, 61 (1), e202113598. https://doi.org/10.1002/anie.202113598.

20

Pigulski, B.; Ximenis, M.; Shoyama, K.; Würthner, F. Synthesis of Polycyclic Aromatic Hydrocarbons by Palladium-Catalysed [3 + 3] Annulation. Org. Chem. Front. 2020, 7 (19), 2925–2930. https://doi.org/10.1039/d0qo00968g.

19

Zhu, C.; Shoyama, K.; Würthner, F. Conformation and Aromaticity Switching in a Curved Non-Alternant sp² Carbon Scaffold. Angew. Chem. Int. Ed. 2020, 59 (48), 21505–21509. https://doi.org/10.1002/anie.202010077.

18

Mahl, M.; Shoyama, K.; Krause, A.; Schmidt, D.; Würthner, F. Base-Assisted Imidization: A Synthetic Method for the Introduction of Bulky Imide Substituents to Control Packing and Optical Properties of Naphthalene and Perylene Imides. Angew. Chem. Int. Ed. 2020, 59 (32), 13401–13405. https://doi.org/10.1002/anie.202004965.

17

Pigulski, B.; Shoyama, K.; Würthner, F. NIR-Absorbing π-Extended Azulene: Non-Alternant Isomer of Terrylene Bisimide. Angew. Chem. Int. Ed. 2020, 59 (37), 15908–15912. https://doi.org/10.1002/anie.202005376.

16

Shoyama, K.; Mahl, M.; Niyas, M. A.; Ebert, M.; Kachler, V.; Keck, C.; Würthner, F. Palladium-Catalyzed [3+2] Annulation of Naphthalimide Acceptors and Thiophene Donors. J. Org. Chem. 2020, 85 (1), 142–149. https://doi.org/10.1021/acs.joc.9b02372.

15

Shoyama, K.; Würthner, F. Synthesis of a Carbon Nanocone by Cascade Annulation. J. Am. Chem. Soc. 2019, 141 (33), 13008–13012. https://doi.org/10.1021/jacs.9b06617.

14

Nowak-Król, A.; Shoyama, K.; Stolte, M.; Würthner, F. Naphthalene and Perylene Diimides – Better Alternatives to Fullerenes for Organic Electronics? Chem. Commun. 2018, 54 (98), 13763–13772. https://doi.org/10.1039/c8cc07640e.

13

Mahl, M.; Shoyama, K.; Rühe, J.; Grande, V.; Würthner, F. Tetrachlorinated Polycyclic Aromatic Dicarboximides: New Electron-Poor π-Scaffolds and NIR Emitters by Palladium-Catalyzed Annulation Reaction. Chem. Eur. J. 2018, 24 (37), 9409–9416. https://doi.org/10.1002/chem.201801191.

12

Shoyama, K.; Mahl, M.; Seifert, S.; Würthner, F. A General Synthetic Route to Polycyclic Aromatic Dicarboximides by Palladium-Catalyzed Annulation Reaction. J. Org. Chem. 2018, 83 (10), 5339–5346. https://doi.org/10.1021/acs.joc.8b00301.

11

Shoyama, K.; Sato, W.; Guo, Y.; Nakamura, E. Effects of Water on the Forward and Backward Conversions of Lead(II) Iodide to Methylammonium Lead Perovskite. J. Mater. Chem. A 2017, 5 (45), 23815–23821. https://doi.org/10.1039/c7ta08042e.

10

Shoyama, K.; Schmidt, D.; Mahl, M.; Würthner, F. Electron-Poor Bowl-Shaped Polycyclic Aromatic Dicarboximides: Synthesis, Crystal Structures, and Optical and Redox Properties. Org. Lett. 2017, 19 (19), 5328–5331. https://doi.org/10.1021/acs.orglett.7b02618.

9

Li, Z.-J.; Wang, S.; Li, S.-H.; Sun, T.; Yang, W.-W.; Shoyama, K.; Nakagawa, T.; Jeon, I.; Yang, X.; Matsuo, Y.; Gao, X. Regiocontrolled Electrosynthesis of [60]Fullerene Bisadducts: Photovoltaic Performance and Crystal Structures of C₆₀ o‑Quinodimethane Bisadducts. J. Org. Chem. 2017, 82 (16), 8676–8685. https://doi.org/10.1021/acs.joc.7b01732.

8

Guo, Y.; Sato, W.; Shoyama, K.; Halim, H.; Itabashi, Y.; Shang, R.; Nakamura, E. Citric Acid Modulated Growth of Oriented Lead Perovskite Crystals for Efficient Solar Cells. J. Am. Chem. Soc. 2017, 139 (28), 9598–9604. https://doi.org/10.1021/jacs.7b03856.

7

Seifert, S.; Schmidt, D.; Shoyama, K.; Würthner, F. Base-Selective Five- versus Six-Membered Ring Annulation in Palladium-Catalyzed C–C Coupling Cascade Reactions: New Access to Electron-Poor Polycyclic Aromatic Dicarboximides. Angew. Chem. Int. Ed. 2017, 56 (26), 7595–7600. https://doi.org/10.1002/anie.201702889.

6

Guo, Y.; Sato, W.; Shoyama, K.; Nakamura, E. Sulfamic Acid-Catalyzed Lead Perovskite Formation for Solar Cell Fabrication on Glass or Plastic Substrates. J. Am. Chem. Soc. 2016, 138 (16), 5410–5416. https://doi.org/10.1021/jacs.6b02130.

5

Seifert, S.; Shoyama, K.; Schmidt, D.; Würthner, F. An Electron-Poor C₆₄ Nanographene by Palladium-Catalyzed Cascade C−C Bond Formation: One-Pot Synthesis and Single-Crystal Structure Analysis. Angew. Chem. Int. Ed. 2016, 55 (22), 6390–6395. https://doi.org/10.1002/anie.201601433.

4

Guo, Y.; Shoyama, K.; Sato, W.; Nakamura, E. Polymer Stabilization of Lead(II) Perovskite Cubic Nanocrystals for Semitransparent Solar Cells. Adv. Energy Mater. 2016, 6 (6), 1502317. https://doi.org/10.1002/aenm.201502317.

3

Guo, Y.^‡; Shoyama, K.^‡; Sato, W.; Matsuo, Y.; Inoue, K.; Harano, K.; Liu, C.; Tanaka, H.; Nakamura, E. Chemical Pathways Connecting Lead(II) Iodide and Perovskite via Polymeric Plumbate(II) Fiber. J. Am. Chem. Soc. 2015, 137 (50), 15907–15914. https://doi.org/10.1021/jacs.5b10599. ^‡ Contributed equally

2

Mitsui, C.; Soeda, J.; Miwa, K.; Shoyama, K.; Ota, Y.; Tsuji, H.; Takeya, J.; Nakamura, E. Single-Crystal Organic Field-Effect Transistors of Naphthodifurans. Bull. Chem. Soc. Jpn. 2015, 88 (6), 776–783. https://doi.org/10.1246/bcsj.20150033. (BCSJ Award Article)

1

Tsuji, H.; Shoyama, K.; Nakamura, E. Anthradifuran, a Furan Analogue of Pentacene, and its Isomers, Exhibiting Solid-State Photoluminescence. Chem. Lett. 2012, 41 (9), 957–959.https://doi.org/10.1246/cl.2012.957.