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Ryuichi Fujita, Miho Hirakawa, Ryoko Oyama, Kyohei Matsuo, [Hironobu Hayashi](https://orcid.org/0000-0002-7872-3052), Mitsuaki Yamauchi, Hiroko Yamada, Naoki Aratani

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[One‐Step Synthesis of a 2,2’‐Directly‐Linked Perylene Dimer from a 2,5,8,11‐Tetraborylated Perylene](https://mdr.nims.go.jp/datasets/3ab2c7ee-e513-4609-b485-0a24f57938af)

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One‐Step Synthesis of a 2,2’‐Directly‐Linked Perylene Dimer from a 2,5,8,11‐Tetraborylated PeryleneOne-Step Synthesis of a 2,2’-Directly-Linked Perylene Dimerfrom a 2,5,8,11-Tetraborylated PeryleneRyuichi Fujita,[a] Miho Hirakawa,[a] Ryoko Oyama,[a] Kyohei Matsuo,[b] Hironobu Hayashi,[c]Mitsuaki Yamauchi,[b] Hiroko Yamada,*[b] and Naoki Aratani*[a]One-step Suzuki-Miyaura cross-coupling reaction of 2,5,8,11-tetra-borylated perylene with 2,6-bis(trifluoromethyl)bromo-benzene gave 2,2’-linked perylene dimer for the first time in7.3% yield under the standard conditions. The single-crystal X-ray structure exhibits three independent dimers in the unit cell,reflecting the low rotational energy around 2,2’-linkage. Excitedstate properties of 2,2’-dimer were compared with the corre-sponding 3,3’-linked congener. The facile synthetic methoddeveloped in this study could be a general route to accesspolycyclic aromatic hydrocarbon oligomers linked at lessreactive positions.Introductionπ-Conjugation of polycyclic aromatic hydrocarbons (PAHs) canbe expanded by ring-fusion or oligomerization, resulting in asignificant effect on photophysical properties such as a long-wavelength shift in the absorption spectrum.[1] In general, whenPAHs are oligomerized at the position having the highestreactivity, the reaction pathway is simple and rapid.[2] Forexample, facile coupling methods based on oxidation reactionshave been developed for the homogeneous oligomerization ofpyrene[3] and porphyrin.[4] On the other hand, to synthesize PAHoligomers linked at positions with low reactivity, it is oftennecessary to take a multi-step route.[5] This is why there are nopractical reports on 2,2’-linked perylene dimers despite theirsymmetric structure.[6]When two 2,6-bis(trifluoromethyl)phenyl groups 2 wereintroduced into bis-borylated naphthalene 1[7] at the 2,7-positions, 2,2’-linked dimer 4 was formed under standardSuzuki-Miyaura cross-coupling conditions in 23% yield, alongwith the corresponding monomer 3 in 53% yield (Scheme 1).[8]We therefore applied this side reaction to synthesize a 2,2’-linked perylene dimer. Consequently, the 2,2’-directly linkedhexaaryl-substituted perylene dimer was obtained from pristineperylene in only two steps. Due to the small coefficients of thefrontier orbitals at the 2,5,8,11-positions of perylene, theelectronic communication between perylenes are expected tobe limited even though the 2,2’-dimer takes co-planar (videinfra). A 3,3’-linked perylene dimer[9] possessing the samesubstituents was also synthesized, and the differences in opticalproperties depending on the bonding positions were com-pared.Results and DiscussionSynthesis2,5,8,11-Tetra-borylated perylene 5 was prepared by theiridium-catalyzed direct borylation of perylene.[10] The Suzuki-Miyaura cross-coupling reaction of 5 with 2,6-bis(trifluoromethyl)bromobenzene 2 not only afforded tetraaryl-substituted perylene monomer 6[8] in 16% but also simulta-neously led to the formation of hexaaryl-substituted perylenedimer 7 in 7.3% yield (Scheme 2). In this reaction, we usedPdCl2(dppf) (20 mol%) and 6 equivalents of 2 in a mixed solvent[a] R. Fujita, M. Hirakawa, Dr. R. Oyama, Prof. Dr. N. ArataniDivision of Materials Science, Nara Institute of Science and Technology(NAIST), 8916–5 Takayama-cho, Ikoma, Nara 630–0192, JapanE-mail: aratani@ms.naist.jp[b] Dr. K. Matsuo, Dr. M. Yamauchi, Prof. Dr. H. YamadaInstitute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611–0011, JapanE-mail: hyamada@scl.kyoto-u.ac.jp[c] Dr. H. HayashiCenter for Basic Research on Materials, National Institute for MaterialsScience (NIMS), 1–2–1 Sengen, Tsukuba, Ibaraki 305–0047, JapanSupporting information for this article is available on the WWW underhttps://doi.org/10.1002/ejoc.202500042© 2025 The Author(s). European Journal of Organic Chemistry published byWiley-VCH GmbH. This is an open access article under the terms of theCreative Commons Attribution Non-Commercial NoDerivs License, whichpermits use and distribution in any medium, provided the original work isproperly cited, the use is non-commercial and no modifications or adap-tations are made.Scheme 1. Synthesis of 2,7-di-substituted naphthalene 3 and 7,7’-di-substi-tuted-2,2’-binaphthyl 4 from 2,7-diboryl naphthalene 1.Wiley VCH Donnerstag, 01.05.20252551 / 399542 [S. 129/133] 1Eur. J. Org. Chem. 2025, 28, e202500042 (1 of 5) © 2025 The Author(s). European Journal of Organic Chemistry published by Wiley-VCH GmbHwww.eurjoc.orgResearch Articledoi.org/10.1002/ejoc.202500042http://orcid.org/0000-0001-9289-0837http://orcid.org/0000-0002-2472-9459http://orcid.org/0000-0002-7872-3052http://orcid.org/0000-0003-0005-5960http://orcid.org/0000-0002-2138-5902http://orcid.org/0000-0002-3181-6526https://doi.org/10.1002/ejoc.202500042http://crossmark.crossref.org/dialog/?doi=10.1002%2Fejoc.202500042&domain=pdf&date_stamp=2025-03-03of 1,4-dioxane and water. The structure of 7 was confirmed bymass spectrometry and 1H- and 19F-NMR spectroscopy (Support-ing Information: SI). High-resolution matrix-assisted laser-desorption/ionization time-of-flight (HR-MALDI-TOF) mass spec-trometry detected the parent ion peak at m/z=1774.2083(calcd for C88H34F36 =1774.2080 [M]+). Notably, the 19F-NMRspectrum of 7 shows three singlet peaks at room temperature,suggesting that 7 is fully co-planar or free-rotating around the2,2’-linkage in solution (Figure S4).It is well known that the homo-coupling reaction in theSuzuki-Miyaura couplings such as polymer synthesis occurs in acertain percentage.[11] A plausible mechanism to form the directlinkage between 2-positions is a concomitant side reaction ofpalladium-catalyzed cross-coupling reaction; the boronic acids(esters) are used as sacrificial nucleophiles, and transmetalationof 2 equivalents of 5 onto Pd(II) followed by reductiveelimination generates Pd(0) species accompanying formation ofa C� C homo-coupling product.[12]For comparison, 3,3’-perylene dimer was prepared from2,5,8-triarylperylene as shown in Scheme 3.[9] Ni(0)-mediatedhomo-coupling reaction of bromoperylene 8[8] afforded 3,3’-perylene dimer 9 in 48% yield. The structure of 9 was alsocharacterized by HR-MALDI-TOF mass spectrometry and 1H- and19F-NMR spectroscopy.Noteworthy here again is the 19F-NMR spectrum. Six singletpeaks are observed at room temperature, indicating that therotation at the 3,3’ linkage is inhibited in solution (Figure S6).Single-Crystal X-Ray AnalysisThe single-crystals suitable for X-ray diffraction were obtainedby vapor diffusion of methanol into a solution of 7 in CH2Cl2(Figure 1).[13] In the crystal, three independent 2,2’-dimers existin the unit cell (Z=12), one of which takes co-planarconfiguration, and the others are perpendicular. The dihedralangles between perylene cores are 3°, 81°, and 87°, respectively.The fact that the dimers have various dihedral angles in thecrystal suggests that the rotational energy of the 2,2’-linkage isconsiderably small.The single-crystals suitable for X-ray diffraction were alsoobtained by vapor diffusion of methanol into a solution of 9 inCH2Cl2 (Figure 2).[13] In case of 3,3’-dimer, only one kind of anindependent molecule was analyzed in the unit cell and thedihedral angle between perylene cores is 86° since the hydro-gen atoms at the peri-positions restrict the rotation of the twoperylenes compared to the 2,2’-perylene dimer. This result isconsistent with the 19F-NMR spectrum in solution (Figure S6).Photophysical PropertiesTo gain insight into the electronic communications betweenperylenes, UV-vis absorption spectra of 6, 7, and 9 in CH2Cl2were measured (Figure 3a). The absorption spectrum of 7showed only a small red-shift relative to that of monomer 6,even though the co-planar configuration of 7, due to the smallcoefficients of the frontier orbitals at the 2-position of perylene.On the other hand, the shape of the red-shifted UV-visabsorption spectrum of 9 was clearly different from those of 6and 7, presumably due to the strong electron correlation viathe 3-position.Photo-excited charge transfer due to “symmetry breaking”between the identical dyes has been studied in detail fordirectly-linked PAH dimers,[9,14] as in the case of 9,9’-anthryl.[15]To evaluate the interaction at the excited states in differentbonding positions, photophysical properties of 7 and 9 weremeasures in cyclohexane, toluene, THF, CHCl3, and CH2Cl2(Figures 3b and c). For the 2,2’-dimer, no significant changeswere observed in either the absorption and fluorescencespectra (Figure 3b). This indicates that the effect of solventpolarity on both the ground and excited states of the moleculeis negligible.UV-vis absorption spectra of 9 are also nearly invariantacross solvents like that of 7 (Figure 3c). Fluorescence spectra,on the other hand, are affected by solvent. A progressive red-shift in the emission wavelength is observed with increasingsolvent polarity, accompanied by a concomitant broadeningScheme 2. One step synthesis of 5,5’,8,8’,11,11’-hexaaryl-2,2’-bisperylene 7from tetraborylperylene 5.Scheme 3. Synthesis of 5,5’,8,8’,11,11’-hexaaryl-3,3’-bisperylene 9 from triar-ylbromoperylene 8.Wiley VCH Donnerstag, 01.05.20252551 / 399542 [S. 130/133] 1Eur. J. Org. Chem. 2025, 28, e202500042 (2 of 5) © 2025 The Author(s). European Journal of Organic Chemistry published by Wiley-VCH GmbHResearch Articledoi.org/10.1002/ejoc.202500042 10990690, 2025, 17, Downloaded from https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202500042 by National Institute For, Wiley Online Library on [24/08/2025]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License(Figure 3c). The spectra indicate that 9 has a nonpolar groundstate and a higher dipole moment in the excited state, eventhough the two constituent chromophores are identical. Similarbehavior is observed for the 9,9’-bianthryl.[15] In fact, theseStokes shifts of the 3,3’-perylene dimer were analyzed usingMataga-Lippert plots with a straight line having a positive slopedue to the effect of solvent relaxation, i. e., charge transfer afterphoto-excitation (Figure S10).We also measured the fluorescence lifetimes of 6, 7, and 9in cyclohexane, toluene, CH2Cl2, CHCl3 and THF, with the resultssummarized in Figures S11–S13 and Table S1. In the case ofmonomer 6, the fluorescence lifetimes were almost constantregardless of the solvents, but in the cases of compounds 7 and9, the fluorescence lifetimes tended to increase as the polarityof the solvent increased. Moreover, the effect was morepronounced for the 3,3’-dimer than for the 2,2’-dimer.The photochemical measurements for 3,3’-dimer with tert-Bu substituents at 8 and 11 positions[9] showed almost the samefluorescence lifetimes. Therefore, the effect of CF3 substituentson CT could be small.In addition, the stability of the perylene dimers in CH2Cl2solution was evaluated by monitoring changes their UV-visabsorption spectra The solutions of 7 and 9 were exposed toLED room light (400 to 700 nm) under air, showing practicallyno degradation after 24 h.Electrochemical MeasurementsCyclic voltammetry (CV) and differential pulse voltammetry(DPV) measurements in CH2Cl2 were performed to investigatethe redox properties of the series of perylene derivatives(Figure 4). The working, counter, and reference electrodes areglassy carbon, Pt wire, and Ag/AgNO3, respectively. With 0.1 MnBu4NPF6 as the electrolyte, the potentials were determinedbased on the ferrocene/ferrocenium (Fc/Fc+) couple. The resultsFigure 1. Single-crystal X-ray structures of three independent 2,2’-perylenedimers 7 in the unit cell. Fluorine atoms are represented by yellow-greencolor. Thermal ellipsoids are scaled at 25% probability.Figure 2. Single-crystal X-ray structure of 9. Fluorine atoms are representedby yellow-green color. Thermal ellipsoids are scaled at 30% probability.Wiley VCH Donnerstag, 01.05.20252551 / 399542 [S. 131/133] 1Eur. J. Org. Chem. 2025, 28, e202500042 (3 of 5) © 2025 The Author(s). European Journal of Organic Chemistry published by Wiley-VCH GmbHResearch Articledoi.org/10.1002/ejoc.202500042 10990690, 2025, 17, Downloaded from https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202500042 by National Institute For, Wiley Online Library on [24/08/2025]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons Licenseare summarized in Figure 4. Reversible oxidation and reductionwaves were observed at 0.84 and � 2.10 V for the monomer 6.The CV of 7 and 9 exhibited two separated reversible oxidationand two reversible reduction waves, at 0.91, 0.78, � 1.98 and� 2.10 V for the dimer 7, and at 0.95, 0.68,� 2.05 and � 2.11 V forthe dimer 9, respectively. The difference between the first (Eox1)and second (Eox2) oxidation potentials of 9 (0.27 V) is muchlarger than that of 7 (0.13 V). On the reduction side, twoseparated waves were also observed, but the difference is notas great as on the oxidation side. Thus, it is again confirmedthat the electronic communication between perylene units inthe 3,3’-dimer is larger than that of the 2,2’-dimer. This alsoevident in the lowering of the first oxidation potential (0.78 V to0.68 V).ConclusionsIn summary, we have succeeded in synthesizing the hexaaryl-substituted 2,2’-perylene dimer 7 in two steps from peryleneeven the coupling was achieved at the less reactive 2-positions.To the best our knowledge, this is the first practical report of2,2’-perylene dimer. The photophysical properties of the 2,2’-perylene dimer were experimentally investigated and comparedwith those of the 3,3’-directly linked perylene dimer. Althoughno significant changes in absorption and fluorescence spectrawere observed in the 2,2’-dimer due to the decoupledelectronic communication, the fluorescence spectra of the 3,3’-dimer showed certain change depending on solvent polarity,indicating intramolecular charge transfer of 9 in the excitedstate.The facile synthetic method developed in this study couldbe a general route to access PAH oligomers linked at lessreactive positions.Supporting Information SummaryFull details of synthesis, additional spectra, details of datacollections are available in the Supporting Information.AcknowledgementsThis work was supported by the Japan Society for thePromotion of Science (JSPS) KAKENHI Grant Nos. JP24K01576Figure 3. (a) UV-vis absorption spectra of 6, 7, and 9 in CH2Cl2. UV-visabsorption (solid line) and fluorescence (broken line) spectra of (b) 7 and (c)9 in various solvents.Figure 4. Cyclic (black line) and differential pulse (red line) voltammogramsof a) 6, b) 7, and c) 9 at a scan rate of 0.1 V/s in CH2Cl2 (0.1 M nBu4NPF6).Wiley VCH Donnerstag, 01.05.20252551 / 399542 [S. 132/133] 1Eur. J. Org. Chem. 2025, 28, e202500042 (4 of 5) © 2025 The Author(s). European Journal of Organic Chemistry published by Wiley-VCH GmbHResearch Articledoi.org/10.1002/ejoc.202500042 10990690, 2025, 17, Downloaded from https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202500042 by National Institute For, Wiley Online Library on [24/08/2025]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License(HH), JP23K26480 (NA), JP24K23087 (RO), JP24H01714 (MY), andJP20H05833 (Transformative Research Areas “Dynamic Exciton”)(HY), and by JST PRESTO grant No. JPMJPR21AC (HH). We thankYoshiko Nishikawa and Shohei Katao (NAIST) for MS measure-ments and X-ray crystallographic analysis, respectively. Thiswork was partly supported by ARIM Program of the Ministry ofEducation, Culture, Sports, Science and Technology (MEXT)(JPMXP1224NR5025).Conflict of InterestsThe authors declare no conflict of interest.Data Availability StatementThe data that support the findings of this study are available inthe supplementary material of this article.Keywords: Cross coupling · Oligomer · One step synthesis ·Symmetry breaking · π-Conjugation[1] J. T. Markiewicz, F. Wudl, ACS Appl. Mater. Interfaces 2015, 7, 28063–28085.[2] a) A. Matsumoto, M. Suzuki, H. Hayashi, D. Kuzuhara, J. Yuasa, T. Kawai,N. Aratani, H. Yamada, Bull. Chem. Soc. Jpn. 2017, 90, 667–677; b) A.Matsumoto, M. Suzuki, H. Hayashi, D. Kuzuhara, J. Yuasa, T. Kawai, N.Aratani, H. Yamada, Chem. Eur. J. 2016, 22, 14462–14466.[3] K. Yamashita, A. Nakamura, K. Sugiura, Chem. Lett. 2015, 44, 303–305.[4] N. Aratani, A. 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RapidCommun. 2015, 36, 231–237; c) F. Lombeck, H. Komber, D. Fazzi, D.Nava, J. Kuhlmann, D. Stegerer, K. Strassel, J. Brandt, A. D. de Zerio Men-daza, C. Müller, W. Thiel, M. Caironi, R. Friend, M. Sommer, Adv. EnergyMater. 2016, 6, 1601232.[12] a) M. Moreno-Mañas, M. Pérez, R. Pleixats, J. Org. Chem. 1996, 61, 2346–2351; b) B. T. Ingoglia, C. C. Wagen, S. L. Buchwald, Tetrahedron 2019,75, 4199–4211.[13] Deposition Numbers2416479 (for 7), 2416480 (for 9) contain thesupplementary crystallographic data for this paper. These data areprovided free of charge by the joint Cambridge Crystallographic DataCentre and Fachinformationszentrum Karlsruhe Access Structuresservice.[14] a) M. T. Whited, N. M. Patel, S. T. Roberts, K. Allen, P. I. Djurovich, S. E.Bradforth, M. E. Thompson, Chem. Commun. 2012, 48, 284–286; b) R. E.Cook, B. T. Phelan, R. J. Kamire, M. B. Majewski, R. M. Young, M. R.Wasielewski, J. Phys. Chem. A 2017, 121, 1607–1615; c) Y. Liu, J. Zhao, A.Iagatti, L. Bussotti, P. Foggi, E. Castellucci, M. D. Donato, K. Han, J. Phys.Chem. C 2018, 122, 2502–2511; d) S. Fang, J. Zhou, X. Zhou, C. Wang, N.Jiang, L. Liu, Z. Xie, J. Phys. Chem. C 2019, 123, 23306–23311; e) J. M.Giaimo, A. V. Gusev, M. R. Wasielewski, J. Am. Chem. Soc. 2002, 124,8530–8531.[15] a) N. Nakashima, M. Murakawa, N. Mataga, Bull. Chem. Soc. Jpn. 1976,49, 854–858; b) J. J. Piet, W. Schuddeboom, B. R. Wegewijs, F. C.Grozema, J. M. Warman, J. Am. Chem. Soc. 2001, 123, 5337–5347; c) H.Yao, T. Okada, N. Mataga, J. Phys. Chem. 1989, 93, 7388–7394; d) R.Komskis, P. Adomėnas, O. Adomėnienė, P. Baronas, T. Serevičius, S.Juršėnas, J. Phys. Chem. C 2019, 123, 27344–27354.Manuscript received: January 14, 2025Revised manuscript received: February 19, 2025Accepted manuscript online: February 21, 2025Version of record online: March 3, 2025Wiley VCH Donnerstag, 01.05.20252551 / 399542 [S. 133/133] 1Eur. J. Org. Chem. 2025, 28, e202500042 (5 of 5) © 2025 The Author(s). 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