Peripherally Donor-Installed 7,8-Diaza[5]helicenes as a Platform for Helical Luminophores

Yuta Ikari; Takahito Kaihara; Shimpei Goto; Marcel Bovenkerk; David C. Grenz; Birgit Esser; Marli Ferreira; Patrycja Stachelek; Przemyslaw Data; Takumu Yoshida; Tomoyuki Ikai; Norimitsu Tohnai; Satoshi Minakata; Youhei Takeda

doi:10.1055/a-1343-5810

Synthesis, Table of Contents

Synthesis 2021; 53(09): 1584-1596
DOI: 10.1055/a-1343-5810

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Peripherally Donor-Installed 7,8-Diaza[5]helicenes as a Platform for Helical Luminophores

Authors

Yuta Ikari

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 5650871, Japan
Takahito Kaihara

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 5650871, Japan
Shimpei Goto

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 5650871, Japan
Marcel Bovenkerk

^bInstitute for Organic Chemistry, University of Freiburg, Alberstraße 21, 79104 Freiburg, Germany
David C. Grenz

^bInstitute for Organic Chemistry, University of Freiburg, Alberstraße 21, 79104 Freiburg, Germany
Birgit Esser∗

^bInstitute for Organic Chemistry, University of Freiburg, Alberstraße 21, 79104 Freiburg, Germany
Marli Ferreira

^cFaculty of Chemistry, Silesian University of Technology, M. Strzody 9, 44-100 Gliwice, Poland
Patrycja Stachelek

^dChemistry Department, Durham University, South Road, Durham DH1 3LE, United Kingdom
Przemyslaw Data∗

^cFaculty of Chemistry, Silesian University of Technology, M. Strzody 9, 44-100 Gliwice, Poland

^eCenter of Polymer and Carbon Materials, Polish Academy of Sciences, M. Curie-Sklodowskiej 34, 41-819 Zabrze, Poland
Takumu Yoshida

^fGraduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
Tomoyuki Ikai

^gDepartment of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan
Norimitsu Tohnai

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 5650871, Japan
Satoshi Minakata

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 5650871, Japan
Youhei Takeda ∗

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 5650871, Japan

Abstract

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Abstract

A new family of emissive donor–acceptor–donor (D-A-D) compounds has been developed by introducing two electron donors into the 7,8-diaza[5]helicene core as a novel helical electron acceptor. The X-ray crystallographic analyses revealed the uniquely twisted and helical structures of these compounds in the solid states. Notably, some D-A-D compounds developed herein display distinct mechanochromic luminescence (MCL) in the solid state, and a D-A-D helicene shows circularly polarized luminescence (CPL) with a relatively high luminescence dissymmetry factor g _lum of ca. 10^–3. Time-resolved spectroscopic analysis revealed the aspects of thermally activated delayed fluorescence characters of the helicenes. Furthermore, the emissive helicenes were applied to organic light-emitting diodes as emitters.

Key words

helical structures - mechanochromism - circularly polarized luminescence - donor-acceptor - charge-transfer - organic light-emitting diodes - amination

Full Text

References

References

1a Saleh N, Shen C, Crassous J. Chem. Sci. 2014; 5: 3680
1b Alliard P, Voituriez A, Marinetti A. Dalton Trans. 2014; 43: 15263

2a Martin RH. Angew. Chem. Int. Ed. 1974; 13: 649
2b Shen Y, Chen C.-F. Chem. Rev. 2012; 112: 1463
2c Gingras M. Chem. Soc. Rev. 2013; 42: 968
2d Gingras M, Félix G, Peresutti R. Chem. Soc. Rev. 2013; 42: 1007
2e Gingras M. Chem. Soc. Rev. 2013; 42: 1051

3a Sánchez-Carnerero EM, Agarrabeitia AR, Moreno F, Maroto BL, Muller G, Ortiz MJ, de la Moya S. Chem. Eur. J. 2015; 21: 13488
3b Tanaka H, Inoue Y, Mori T. ChemPhotoChem 2018; 2: 386
3c Zhao W.-L, Li M, Lu H.-Y, Chen C.-F. Chem. Commun. 2019; 55: 13793

4a Sapir M, Donckt EV. Chem. Phys. Lett. 1975; 36: 108
4b Schmidt K, Brovelli S, Coropceanu V, Beljonne D, Cornil J, Bazzini C, Caronna C, Tubino R, Meinardi F, Shuai Z, Brédas J.-L. J. Phys. Chem. A 2007; 111: 10490

5a Nijegorodov NI, Downey WS. J. Phys. Chem. 1994; 98: 5639
5b Beljonne D, Shuai Z, Pourtois G, Bredas JL. J. Phys. Chem. A 2001; 105: 3899

6 Sakai H, Kubota T, Yuasa J, Araki Y, Sakanoue T, Takenobu T, Wada T, Kawai T, Hasobe T. J. Phys. Chem. C 2016; 120: 7860

7a Kubo H, Hirose T, Matsuda K. Org. Lett. 2017; 19: 1776
7b Zhao Z.-H, Zhang M.-Y, Liu D.-H, Zhao C.-H. Org. Lett. 2018; 20: 7590
7c Jia X, Nitsch J, Ji L, Wu Z, Friedrich A, Kerner F, Moos M, Lambert C, Marder TB. Chem. Eur. J. 2019; 25: 10845

8 Klimash A, Pander P, Klooster WT, Coles SJ, Data P, Dias FB, Skabara PJ. J. Mater. Chem. C 2018; 6: 10557
9 Data P, Takeda Y. Chem. Asian J. 2019; 14: 1613
10 Takeda Y, Okazaki M, Minakata S. Chem. Commun. 2014; 50: 10291

11a Data P, Pander P, Okazaki M, Takeda Y, Minakata S, Monkman AP. Angew. Chem. Int. Ed. 2016; 55: 5739
11b Okazaki M, Takeda Y, Data P, Pander P, Higginbotham H, Monkman AP, Minakata S. Chem. Sci. 2017; 8: 2677
11c Takeda Y, Kaihara T, Okazaki M, Higginbotham H, Data P, Tohnai N, Minakata S. Chem. Commun. 2018; 54: 6847
11d Data P, Okazaki M, Minakata S, Takeda Y. J. Mater. Chem. C 2019; 7: 6616
11e Takeda Y, Mizuno H, Okada Y, Okazaki M, Minakata S, Penfold T, Fukuhara G. ChemPhotoChem 2019; 3: 1203
11f Izumi S, Higginbotham HF, Nyga A, Stachelek P, Tohnai N, de Silva P, Data P, Takeda Y, Minakata S. J. Am. Chem. Soc. 2020; 142: 1482
11g Yamagishi H, Nakajima S, Yoo J, Okazaki M, Takeda Y, Minakata S, Albrecht K, Yamamoto K, Badía-Domínguez I, Oliva MM, Delgado CR, Ikemoto Y, Sato H, Imoto K, Nakagawa K, Tokoro H, Ohkoshi S.-i, Yamamoto Y. Commun. Chem. 2020; 3: 118
11h Takeda Y, Data P, Minakata S. Chem. Commun. 2020; 56: 8884

12 Meisenheimer J, Witte K. Ber. Dtsch. Chem. Ges. 1903; 36: 4153
13 Greiner G, Rau H, Bonneau R. J. Photochem. Photobiol. A: Chem. 1996; 95: 115
14 Takeda Y, Okazaki M, Maruoka Y, Minakata S. Beilstein J. Org. Chem. 2015; 11: 9
15 Caronna T, Castiglione F, Famulari A, Fontana F, Malpezzi L, Mele A, Mendola D, Sora IN. Molecules 2012; 17: 463
16 Kuroda R. J. Chem. Soc., Perkin Trans. 2 1982; 789

17a Otani T, Tsuyuki A, Iwachi T, Someya S, Tateno K, Kawai H, Saito T, Kanyiva KS, Shibata T. Angew. Chem. Int. Ed. 2017; 56: 3906
17b Kaiser FP, Nečas D, Cadart T, Gyepes R, Císařová I, Mosinger J, Pospíšil L, Kotora M. Angew. Chem. Int. Ed. 2019; 58: 17169

18 Hoche J, Schulz A, Dietrich LM, Humeniuk A, Stolte M, Schmidt D, Brixner T, Wurthner F, Mitric R. Chem. Sci. 2019; 10: 11013
19 Chen Z, Ho C.-L, Wang L, Wong W.-Y. Adv. Mater. 2020; 32: 1903269/1
20 Zhang Y, Wang K, Zhuang G, Xie Z, Zhang C, Cao F, Pan G, Chen H, Zou B, Ma Y. Chem. Eur. J. 2015; 21: 2474
21 Goedicke C, Stegemeyer H. Tetrahedron Lett. 1970; 11: 937
22 Barroso J, Cabellos JL, Pan S, Murillo F, Zarate X, Fernandez-Herrera MA, Merino G. Chem. Commun. 2018; 54: 188
23 The influence of optical anisotropy on the films was confirmed to be almost negligible (Figure S8 in the ESI). Imperfect mirror-imaged CPL spectra were probably due to inhomogeneity of the films.
24 Lim YK, Jung J.-W, Lee H, Cho C.-G. J. Org. Chem. 2004; 69: 5778

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