Catalytic C–H Arylation of Tetrathiafulvalenes for the Synthesis of Functional Materials

Hideki Yorimitsu; Aya Yoshimura; Yohji Misaki

doi:10.1055/s-0040-1707256

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(22): 3326-3336
DOI: 10.1055/s-0040-1707256

short review

Catalytic C–H Arylation of Tetrathiafulvalenes for the Synthesis of Functional Materials

Hideki Yorimitsu ∗

^aDepartment of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan eMail: yori@kuchem.kyoto-u.ac.jp

,

Aya Yoshimura

^bDepartment of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan

^cResearch Unit for Power Generation and Storage Materials, Ehime University, Matsuyama, Ehime 790-8577, Japan

,

Yohji Misaki

^bDepartment of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan

^cResearch Unit for Power Generation and Storage Materials, Ehime University, Matsuyama, Ehime 790-8577, Japan

^dResearch Unit for Development of Organic Superconductors, Ehime University, Matsuyama, Ehime 790-8577, Japan

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Abstract

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Abstract

Sulfur-containing functional π-conjugated cores play key roles in materials science, mostly due to their unique electrochemical and photophysical properties. Among these, the excellent electron donor tetrathiafulvalene (TTF) has occupied a central position since the emergence of organic electronics. Peripheral C–H modification of this highly useful sulfur-containing motif has resulted in the efficient creation of new molecules that expand the applications of TTFs. This Short Review begins with the development of the palladium-catalyzed direct C–H arylation of TTF. Subsequently, it summarizes the applications of this efficient C–H transformation for the straightforward synthesis of useful TTF derivatives that are employed in a variety of research fields, demonstrating that the development of a new reaction can have a significant impact on chemical science.

1 Introduction

2 Development of the Palladium-Catalyzed Direct C–H Arylation of TTF

3 Synthesis of TTF-Based Tetrabenzoic Acid and Tetrapyridine for MOFs

4 Synthesis of TTF-Based Tetrabenzaldehyde and Tetraaniline for COFs

5 Tetraarylation of TTFAQ

6 Synthesis of Multistage-Redox TTF Derivatives

7 Miscellaneous Examples

8 Conclusions

Key words

C–H arylation - tetrathiafulvalene - sulfur - palladium catalysis - metal-organic framework - covalent organic framework - supramolecular chemistry - redox-active material

Volltext

Referenzen

References

1a Zhang G, Zhao J, Chow PC. Y, Jiang K, Zhang J, Zhu Z, Zhang J, Huang F, Yan H. Chem. Rev. 2018; 118: 3447
1b Cheng P, Li G, Zhang X, Yang Y. Nat. Photonics 2018; 12: 131
1c Nielsen CB, Holliday S, Chen H.-Y, Cryer SJ, McCulloch I. Acc. Chem. Res. 2015; 48: 2803
1d Mishra A, Bäuerle P. Angew. Chem. Int. Ed. 2012; 51: 2020
1e Lin Y, Li Y, Zhan X. Chem. Soc. Rev. 2012; 41: 4245
1f Wang C, Dong H, Hu W, Liu Y, Zhu D. Chem. Rev. 2012; 112: 2208
1g Figueira-Duarte TM, Müllen K. Chem. Rev. 2011; 111: 7260
1h Zhan X, Facchetti A, Barlow S, Marks TJ, Ratner MA, Wasielewski MR, Marder SR. Adv. Mater. 2011; 23: 268
1i Allard S, Forster M, Souharce B, Thiem H, Scherf U. Angew. Chem. Int. Ed. 2008; 47: 4070

2a Takimiya K, Nakano M. Bull. Chem. Soc. Jpn. 2018; 91: 121
2b Turkoglu G, Cinar ME, Ozturk T. Top. Curr. Chem. 2017; 375: 84
2c Takimiya K, Osaka I, Mori T, Nakano M. Acc. Chem. Res. 2014; 47: 1493
2d Takimiya K, Shinamura S, Osaka I, Miyazaki E. Adv. Mater. 2011; 23: 4347
2e Iwanaga T, Yamada Y, Yamauchi T, Misaki Y, Inoue M, Yamada H. Chem. Lett. 2018; 47: 760 ; and references cited therein

3a TTF Chemistry . Yamada J, Sugimoto T. Kodansha-Springer; Tokyo: 2004
3b Hasegawa M, Iyoda M. In Organic Redox Systems . Nishinaga T. Wiley; New Jersey: 2016. Chap. 4, 89
3c Segura JL, Martín N. Angew. Chem. Int. Ed. 2001; 40: 1372
3d Bendikov M, Wudl F, Perepichka DF. Chem. Rev. 2004; 104: 4891
3e Yamada J, Akutsu H, Nishikawa H, Kikuchi K. Chem. Rev. 2004; 104: 5057
3f Iyoda M, Hasegawa M, Miyake Y. Chem. Rev. 2004; 104: 5085
3g Jérome D. Chem. Rev. 2004; 104: 5565
3h Gorgues A, Hudhomme P, Sallé M. Chem. Rev. 2004; 104: 5151
3i Otsubo T, Takimiya K. Bull. Chem. Soc. Jpn. 2004; 77: 43
3j Saito G, Yoshida Y. Bull. Chem. Soc. Jpn. 2007; 80: 1
3k Misaki Y. Sci. Technol. Adv. Mater. 2009; 10: 024301
3l Canevet D, Sallé M, Zhang G, Zhang D, Zhu D. Chem. Commun. 2009; 2245
3m Lorcy D, Bellec N, Fourmigué M, Avarvari N. Coord. Chem. Rev. 2009; 253: 1398
3n Bergkamp JJ, Decurtins S, Liu S.-X. Chem. Soc. Rev. 2015; 44: 863
3o Pop F, Avarvari N. Chem. Commun. 2015; 52: 7906

4a Nishihara Y. Applied Cross-Coupling Reactions . Springer; Heidelberg: 2013
4b Science of Synthesis, Cross Coupling and Heck-Type Reactions, Vol. 1, C–C Cross Coupling Using Organometallic Partners. Molander GA, Larhed M, Wolfe JP. Thieme; Stuttgart: 2013
4c Metal-Catalyzed Cross-Coupling Reactions and More . de Meijere A, Bräse S, Oestreich M. Wiley-VCH; Weinheim: 2014
4d Xu S, Kim EH, Wei A, Negishi E.-i. Sci. Tech. Adv. Mater. 2014; 15: 0442010
4e Zani L, Dessì A, Franchi D, Calamante M, Reginato G, Mordini A. Coord. Chem. Rev. 2019; 392: 177

For selected books, see:

5a Activation of Unreactive Bonds and Organic Synthesis. Murai S. Springer; Heidelberg: 1999
5b Hartung CG, Snieckus V. In Modern Arene Chemistry, Chap. 10 . Astruc D. Wiley-VCH; Weinheim: 2002: 330
5c Activation and Functionalization of C–H Bonds . Goldberg KI, Goldman AS. Oxford University Press; Oxford: 2004
5d Handbook of C–H Transformations . Dyker G. Wiley-VCH; Weinheim: 2005
5e Directed Metalation . Chatani N. Springer; Heidelberg: 2007
5f C–H Activation . Yu J.-Q, Shi Z. Springer; Heidelberg: 2010
5g Science of Synthesis, Cross Coupling and Heck-Type Reactions, Vol. 3, Metal-Catalyzed Heck-Type Reactions and C—C Cross Coupling via C–H Activation. Molander GA, Larhed M, Wolfe J. Thieme; Stuttgart: 2013
5h C–H Bond Activation in Organic Synthesis . Li JJ. CRC Press; Boca Raton: 2015
5i Science of Synthesis, Catalytic Transformations via C–H Activation, Vol. 1. Yu J.-Q. Thieme; Stuttgart: 2015
5j Science of Synthesis, Catalytic Transformations via C–H Activation, Vol. 2. Yu J.-Q. Thieme; Stuttgart: 2015
5k C–H Bond Activation and Catalytic Functionalization, Vol. I. Dixneuf PH, Doucet H. Springer; Heidelberg: 2016
5l C–H Bond Activation and Catalytic Functionalization, Vol. II. Dixneuf PH, Doucet H. Springer; Heidelberg: 2016

For selected reviews, see:

6a Raj S, Ano Y, Chatani N. Chem. Rev. 2020; 120: 1788
6b Zhao Q, Meng G, Nolan SP, Szostak M. Chem. Rev. 2020; 120: 1981
6c Kuang G, Liu G, Zhang X, Lu N, Peng Y, Xiao Q, Zhou Y. Synthesis 2020; 52: 993
6d Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
6e Kuroda Y, Nakao Y. Chem. Lett. 2019; 48: 1092
6f Murai M, Takai K. Synthesis 2019; 51: 40
6g Antermite D, Bull JA. Synthesis 2019; 51: 3171
6h Le Bras J, Muzart J. Synthesis 2019; 51: 2871
6i Maraswami M, Loh T.-P. Synthesis 2019; 51: 1049
6j Kancherla S, Jørgensen KB, Fernández-Ibáñez M. Á. Synthesis 2019; 51: 643
6k Sambiagio C, Schönbauer D, Blieck R, Dao-Huy T, Pototschnig G, Schaaf P, Wiesinger T, Zia MF, Wencel-Delord J, Besset T, Maes BU. W, Schnürch M. Chem. Soc. Rev. 2018; 47: 6603
6l Minami Y, Hiyama T. Chem. Lett. 2018; 47: 1
6m Li Z.-K, Jia X.-S, Yin L. Synthesis 2018; 50: 4165
6n Zhou W.-J, Zhang Y.-H, Gui Y.-Y, Sun L, Yu D.-G. Synthesis 2018; 50: 3359
6o Verbitskiy EV, Rusinov GL, Chupakhin ON, Charushin VN. Synthesis 2018; 50: 193
6p Chatani N. Bull. Chem. Soc. Jpn. 2018; 91: 211
6q Yoshino T, Matsunaga S. Asian J. Org. Chem. 2018; 7: 1193
6r Kommagalla Y, Chatani N. Coord. Chem. Rev. 2017; 350: 117
6s Shang R, Ilies L, Nakamura E. Chem. Rev. 2017; 117: 9086
6t Murakami K, Yamada S, Kaneda T, Itami K. Chem. Rev. 2017; 117: 9302
6u Fuse S, Morita T, Nakamura H. Synthesis 2017; 49: 2351
6v Yoshino T, Matsunaga S. Adv. Synth. Catal. 2017; 359: 1245
6w Yamaguchi J, Itami K. Bull. Chem. Soc. Jpn. 2017; 90: 367
6x Gensch T, Hopkinson MN, Glorius F, Wencel-Delord J. Chem. Soc. Rev. 2016; 45: 2900
6y Davies HM. L, Morton D. J. Org. Chem. 2016; 81: 343
6z Bheeter CB, Chen L, Soulé J.-F, Doucet H. Catal. Sci. Technol. 2016; 6: 2005
6aa Miao J, Ge H. Eur. J. Org. Chem. 2015; 7859
6ab Daugulis O, Roane J, Tran LD. Acc. Chem. Res. 2015; 48: 1053
6ac Chen Z, Wang B, Zhang J, Yu W, Liu Z, Zhang Y. Org. Chem. Front. 2015; 2: 1107
6ad Iwai T, Sawamura M. ACS Catal. 2015; 5: 5031
6ae Castro LC. M, Chatani N. Chem. Lett. 2015; 44: 410
6af Rossi R, Bellina F, Lessi M, Manzini C. Adv. Synth. Catal. 2014; 356: 17
6ag El Kazzouli S, Koubachi J, El Brahmi N, Guillaumet G. RSC Adv. 2015; 5: 15292
6ah Giri R, Thapa S, Kafle A. Adv. Synth. Catal. 2014; 356: 1395
6ai Rossi R, Bellina F, Lessi M, Manzini C, Perego LA. Synthesis 2014; 46: 2833
6aj Rouquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
6ak Shibahara F, Murai T. Asian J. Org. Chem. 2013; 2: 624
6al Nishino M, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2013; 52: 4457
6am Yamaguchi J, Muto K, Itami K. Eur. J. Org. Chem. 2013; 19
6an Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
6ao Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
6ap Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
6aq Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
6ar McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
6as Nakao Y. Synthesis 2011; 3209
6at Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
6au Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
6av Satoh T, Miura M. Chem. Eur. J. 2010; 16: 11212
6aw Roger J, Gottumukkala AL, Doucet H. ChemCatChem 2010; 2: 20
6ax Kulkarni AA, Daugulis O. Synthesis 2009; 4087
6ay Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
6az Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
6ba Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
6bb Kakiuchi F, Kochi T. Synthesis 2008; 3013
6bc Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
6bd Kakiuchi F, Chatani N. Adv. Synth. Catal. 2003; 345: 1077
6be Ishiyama T, Miyaura N. J. Organomet. Chem. 2003; 680: 3
6bf Kakiuchi F, Murai S. Acc. Chem. Res. 2002; 35: 826
6bg Jia C, Kitamura T, Fujiwara Y. Acc. Chem. Res. 2001; 34: 633
6bh Shilov AE, Shul’pin GB. Chem. Rev. 1997; 97: 2879

For reviews on C–H functionalization reactions for the synthesis of discrete π-conjugated materials, see:

7a Ito H, Segawa Y, Murakami K, Itami K. J. Am. Chem. Soc. 2019; 141: 3
7b Ito H, Ozaki K, Itami K. Angew. Chem. Int. Ed. 2017; 56: 11144
7c Hiroto S, Miyake Y, Shinokubo H. Chem. Rev. 2017; 117: 2910
7d Besson T, Fruit C. Synthesis 2016; 48: 3879
7e Shi Y, Ni Z, Zhen Y, Dong H, Hu W. Chin. J. Org. Chem. 2016; 36: 1741
7f Kuninobu Y, Sueki S. Synthesis 2015; 47: 3823
7g Shinokubo H. Proc. Jpn. Acad., Ser. B 2014; 90: 1
7h Wencel-Delord J, Glorius F. Nat. Chem. 2013; 5: 369
7i Yorimitsu H, Osuka A. Asian J. Org. Chem. 2013; 2: 356
7j Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
7k Shinokubo H, Osuka A. Chem. Commun. 2009; 1011

For reviews on C–H arylation reactions for the synthesis of polymers, see:

8a Amna B, Siddiqi HM, Hassan A, Ozturk T. RSC Adv. 2020; 10: 4322
8b Blaskovits JT, Leclerc M. Macromol. Rapid Commun. 2019; 40: 1800512
8c Kuwabara J, Kinbara T. Bull. Chem. Soc. Jpn. 2019; 92: 152
8d Wakioka M, Ozawa F. Asian J. Org. Chem. 2018; 7: 1206
8e Gobalasingham NS, Thompson BC. Prog. Polym. Sci. 2018; 83: 135
8f Yang Y, Nishiura M, Wang H, Hou Z. Coord. Chem. Rev. 2018; 376: 506
8g Bura T, Blaskovits JT, Leclerc M. J. Am. Chem. Soc. 2016; 138: 10056
8h Pouliot J.-R, Grenier F, Blaskovits JT, Beaupré S, Leclerc M. Chem. Rev. 2016; 116: 14225
8i Okamoto K, Zhang J, Housekeeper JB, Marder SR, Luscombe CK. Macromolecules 2013; 46: 8059
8j Mercier LG.. Leclerc M. Acc. Chem. Res. 2013; 46: 1597

For selected examples, see:

9a Iyoda M, Kuwatani Y, Ueno N, Oda M. J. Chem. Soc., Chem. Commun. 1992; 158
9b Iyoda M, Fukuda M, Yoshida M, Sasaki S. Chem. Lett. 1994; 2369
9c Kux U, Iyoda M. Chem. Lett. 1994; 2327
9d Iyoda M, Fukuda M, Sasaki S, Yoshida M. Synth. Met. 1995; 70: 1171
9e Nakatsuji S, Satoki S, Suzuki K, Enoki T, Kinoshita N, Anzai H. Synth. Met. 1995; 71: 1819
9f Skabara PJ, Müllen K, Bryce MR, Howard JA. K, Batsanov AS. J. Mater. Chem. 1998; 8: 1719
9g Nakazaki J, Matsushita MM, Izuoka A, Sugawara T. Tetrahedron Lett. 1999; 40: 5027
9h Iyoda M, Hasegawa M, Kuwatani Y, Nishikawa H, Fukami K, Nagase S, Yamamoto G. Chem. Lett. 2001; 1146
9i Moore AJ, Batsanov AS, Bryce MR, Howard JA. K, Khodorkovsky V, Shapiro L, Shames A. Eur. J. Org. Chem. 2001; 73
9j Bouguessa S, Gouasmia AK, Golhen S, Ouahab L, Fabre JM. Tetrahedron Lett. 2003; 44: 9275
9k Murata T, Morita Y, Fukui K, Sato K, Shiomi D, Takui T, Maesato M, Yamochi H, Saito G, Nakasuji K. Angew. Chem. Int. Ed. 2004; 43: 6343
9l Nishida S, Morita Y, Fukui K, Sato K, Shiomi D, Takui T, Nakasuji K. Angew. Chem. Int. Ed. 2005; 44: 7277
9m Wang L, Zhang B, Zhang J. Inorg. Chem. 2006; 45: 6860
9n Kanato H, Narutaki M, Takimiya K, Otsubo T, Harima Y. Chem. Lett. 2006; 35: 668
9o Chahma M, Wang X, van der Est A, Pilkington M. J. Org. Chem. 2006; 71: 2750
9p Lamère JF, Malfant I, Sornia-Saquet A, Lacroix PG, Fabre JM, Kaboub L, Abbaz T, Gouasmia AK, Asselberghs I, Clays K. Chem. Mater. 2007; 19: 805
9q Abbz T, Gouasmia A.-K, Fujiwara H, Hiraoka T, Sugimoto T, Taillefer M, Fabre J.-M. Synth. Met. 2007; 157: 508
9r Murata T, Morita Y, Yakiyama Y, Fukui K, Yamochi H, Saito G, Nakasuji K. J. Am. Chem. Soc. 2007; 129: 10837
9s Fujiwara H, Sugishima Y, Tsujimoto K. Tetrahedron Lett. 2008; 49: 7200
9t Wang Y, Cui S, Li B, Zhang J, Zhang Y. Cryst. Growth Des. 2009; 9: 3855
9u Carmieli R, Mi Q, Ricks AB, Giacobbe EM, Mickley SM, Wasielewski MR. J. Am. Chem. Soc. 2009; 131: 8372
9v Riobé F, Avarvari N, Grosshans P, Sidorenkova H, Berclaz T, Geoffroy M. Phys. Chem. Chem. Phys. 2010; 12: 9650
9w Bouguessa S, Gouasmia AK, Ouahab L, Golhen S, Fabre J.-M. Synth. Met. 2010; 160: 361
9x Lee SC, Ueda A, Kamo H, Takahashi K, Uruichi M, Yamamoto K, Yakushi K, Nakao A, Kumai R, Kobayashi K, Nakao H, Murakami Y, Mori H. Chem. Commun. 2012; 48: 8673
9y Pointillart F, Bourdolle A, Cauchy T, Maury O, Gal YL, Golhen S, Cador O, Ouahab L. Inorg. Chem. 2012; 51: 978
9z Hasegawa M, Daigoku K, Hashimoto K, Nishikawa H, Iyoda M. Bull. Chem. Soc. Jpn. 2012; 85: 51
9aa Poddutoori PK, Zarrabi N, Moiseev AG, Gumbau-abrisa R, Vassiliev S, van der Est A. Chem. Eur. J. 2013; 19: 3148
9ab Tsujimoto K, Ogasawara R, Fujiwara H. Tetrahedron Lett. 2013; 54: 1251
9ac Lee SC, Ueda A, Nakao A, Kumai R, Nakao H, Murakami Y, Mori H. Chem. Eur. J. 2014; 20: 1909
9ad Tsunashima R, Iwamoto Y, Baba Y, Kato C, Ichihashi K, Nishihara S, Inoue K, Ishiguro K, Song Y.-F, Akutagawa T. Angew. Chem. Int. Ed. 2014; 53: 11228
9ae Hayward JJ, Gumbau-Brisa R, Alberola A, Clarke CS, Rawson JM, Pilkington M. CrystEngComm 2014; 16: 7268
9af Kobayakawa K, Hasegawa M, Sasaki H, Endo J, Matsuzawa H, Sako K, Yoshida J, Mazaki Y. Chem. Asian J. 2014; 9: 2751
9ag Geng Y, Pop F, Yi C, Avarvari N, Grätzel M, Decurtins S, Liu S.-X. New. J. Chem. 2014; 38: 3269
9ah Ayadi A, Alamy AE, Alévêque O, Allain M, Zouari N, Bouachrine M, El-Ghayoury A. Beilstein J. Org. Chem. 2015; 11: 1379
9ai Nafe J, Auras F, Karaghiosoff K, Bein T, Knochel P. Org. Lett. 2015; 17: 5356
9aj Nafe J, Knochel P. Synthesis 2016; 48: 103
9ak Okino R, Yamaguchi M, Fujiwara H. Dalton Trans. 2017; 46: 4912
9al Kanetou T, Tsunashima R, Hoshino N, Akutagawa T. RSC Adv. 2017; 7: 6236
9am Kishi Y, Cornet L, Pointillart F, Riobé F, Lefeuvre B, Cador O, Guennic BL, Maury O, Fujiwara H, Ouahab L. Eur. J. Org. Chem. 2018; 458
9an Stetsiuk O, Petrusenko SR, El-Ghayoury A, Kokozay VN, Avarvari N. Inorg. Chim. Acta 2018; 475: 172
9ao Zarrabi N, Lim GN, Bayard BJ, D’Souza F, Poddutoori PK. Phys. Chem. Chem. Phys. 2019; 21: 19612
9ap Yoshimura A, Kimura H, Handa A, Hashimoto N, Yano M, Mori S, Shirahata T, Hayashi M, Misaki Y. Tetrahedron Lett. 2020; 61: 151724

10 Mitamura Y, Yorimitsu H, Oshima K, Osuka A. Chem. Sci. 2011; 2: 2017

11a Dyker G, Heiermann J, Miura M, Inoh J.-I, Pivsa-Art S, Satoh T, Nomura M. Chem. Eur. J. 2000; 6: 3426
11b Miura M, Pivsa-Art S, Dyker G, Heiermann J, Satoh T, Nomura M. Chem. Commun. 1998; 1889

12 Dolphin D, Pegg W, Wirz P. Can. J. Chem. 1974; 52: 4078

13a Lapointe D, Fagnou K. Chem. Lett. 2010; 39: 1118
13b Lafrance M, Fagnou K. J. Am. Chem. Soc. 2006; 128: 16496
13c García-Cuadrado D, Braga AA. C, Maseras F, Echavarren AM. J. Am. Chem. Soc. 2006; 128: 1066
13d García-Cuadrado D, de Mendoza P, Braga AA. C, Maseras F, Echavarren AM. J. Am. Chem. Soc. 2007; 129: 6880

14 Netherton MR, Fu GC. Org. Lett. 2001; 3: 4295

15a Lengthy synthesis: Charlton A, Underhill AE, Williams G, Kalaji M, Murphy PJ, Hibbs DE, Hursthouse MB, Malik KM. A. Chem. Commun. 1996; 2423
15b Condensation of diarylacetylene with carbon disulfide under 4500 atm: Nagawa T, Zama Y, Okamoto Y. Bull. Chem. Soc. Jpn. 1984; 57: 2035

16 Ueno R, Fujino D, Yorimitsu H, Osuka A. Chem. Eur. J. 2013; 19: 7156

17a Sun L, Campbell MG, Dincă M. Angew. Chem. Int. Ed. 2016; 55: 3566
17b Wang H.-Y, Cui L, Xie J.-Z, Leong CF, D’Alessandro DM, Zuo J.-L. Coord. Chem. Rev. 2017; 345: 342
17c Jana A, Bähring S, Ishida M, Goeb S, Canevet D, Sallé M, Jeppesen JO, Sessler JL. Chem. Soc. Rev. 2018; 47: 5614
17d Calbo J, Golomb MJ, Walsh A. J. Mater. Chem. A 2019; 7: 16571

18 Narayan TC, Miyakai T, Seki S, Dincă M. J. Am. Chem. Soc. 2012; 134: 12932

19a Park SS, Hontz ER, Sun L, Hendon CH, Walsh A, Van Voorhis T, Dincă M. J. Am. Chem. Soc. 2015; 137: 1774
19b Chen B, Lv Z.-P, Leong CF, Zhao Y, D’Alessandro DM, Zuo J.-L. Cryst. Growth. Des. 2015; 15: 1861
19c Sun L, Park SS, Sheberla D, Dincă M. J. Am. Chem. Soc. 2016; 138: 14772
19d Park SS, Hendon CH, Fielding AJ, Walsh A, O’Keeffe M, Dincă M. J. Am. Chem. Soc. 2017; 139: 3619
19e Su J, Yuan S, Wang H.-Y, Huang L, Ge J.-Y, Joseph E, Qin J, Cagin T, Zuo J.-L, Zhou H.-C. Nat. Commun. 2017; 8: 2008
19f Park SS, Rieth AJ, Hendon CH, Dincă M. J. Am. Chem. Soc. 2018; 140: 2016
19g Souto M, Romero J, Calbo J, Vitórica-Yrezábal IJ, Zafra JL, Casado J, Ortí E, Walsh A, Espallargas GM. J. Am. Chem. Soc. 2018; 140: 10562
19h Souto M, Santiago-Portillo A, Palomino M, Vitórica-Yrezábal IJ, Vieira BJ. C, Waerenborgh JC, Valencia S, Navalón S, Rey F, García H, Mínguez Espallargas G. Chem. Sci. 2018; 9: 2413
19i Leong CF, Wang C.-H, Ling CD, D’Alessandro DM. Polyhedron 2018; 154: 334
19j Su J, Hu T.-H, Murase R, Wang H.-Y, D’Alessandro DM, Kurmoo M, Zuo J.-L. Inorg. Chem. 2019; 58: 3698
19k Pattengale B, Neu J, Ostresh S, Hu G, Spies JA, Okabe R, Brudvig GW, Schmuttenmaer CA. J. Am. Chem. Soc. 2019; 141: 9793
19l Castells-Gil J, Mañas-Valero S, Vitórica-Yrezábal IJ, Ananias D, Rocha J, Santiago R, Bromley ST, Baldoví JJ, Coronado E, Souto M, Mínguez Espallargas G. Chem. Eur. J. 2019; 25: 12636
19m Cadiau A, Xie LS, Kolobov N, Shkurenko A, Qureshi M, Tchalala MR, Park SS, Bavykina A, Eddaoudi M, Dincă M, Henden CH, Gascon J. Chem. Mater. 2020; 32: 97
19n Wang F, Wang J, Maehrlein SF, Ma Y, Liu F, Zhu X.-Y. J. Phys. Chem. Lett. 2020; 11: 762
19o Su J, He W, Li X.-M, Sun L, Wang H.-Y, Lan Y.-Q, Ding M, Zuo J.-L. Matter 2020; 2: 711

20a Hisaki I, Affendy EN. Q, Tohnai N. CrystEngComm 2017; 19: 4892
20b Zheng X, Xiao N, Long Z, Wang L, Ye F, Fang J, Shen L, Xiao X. Synth. Met. 2020; 263: 116365

21 Lv Z.-P, Chen B, Wang H.-Y, Wu Y, Zuo J.-L. Small 2015; 11: 3597
22 Liu L, Zhou S, Zhao C, Jiu T, Bi F, Jian H, Zhao M, Zhang G, Wang L, Li F, Xiao X. J. Energy Chem. 2020; 42: 210
23 Vajpayee V, Bivaud S, Goeb S, Croué V, Allain M, Popp BV, Garci A, Therrien B, Sallé M. Organometallics 2014; 33: 1651 . In this paper, ruthenium complexes of tetra(3-pyridyl) 1m were also reported
24 Goeb S, Bivaud S, Croué V, Vajpayee V, Allain M, Sallé M. Materials 2014; 7: 611
25 Tzeng B.-C, Hsiao Y.-J, Lee G.-H, Wang H.-Y, Leong CF, D’Alessandro DM, Zuo J.-L. Dalton Trans. 2019; 48: 7946

26a Wang H.-Y, Wu Y, Leong CF, D’Alessandro DM, Zuo J.-L. Inorg. Chem. 2015; 54: 10766
26b Wang H.-Y, Ge J.-Y, Hua C, Jiao C.-Q, Wu Y, Leong CF, D’Alessandro DM, Liu T, Zuo J.-L. Angew. Chem. Int. Ed. 2017; 56: 5465
26c Wang H.-Y, Su J, Ma J.-P, Yu F, Leong CF, D’Alessandro DM, Kurmoo M, Zuo J.-L. Inorg. Chem. 2019; 58: 8657
26d Yu Q, Su J, Ma J.-P, Leong CF, D’Alessandro DM, Wang H.-Y, Kurmoo M, Zuo J.-L. Cryst. Growth Des. 2019; 19: 3012

27 Jin S, Sakurai T, Kowalczyk T, Dalapati S, Xu F, Wei H, Chen X, Gao J, Seki S, Irle S, Jiang D. Chem. Eur. J. 2014; 20: 14608
28 Ding H, Li Y, Hu H, Sun Y, Wang J, Wang C, Wang C, Zhang G, Wang B, Xu W, Zhang D. Chem. Eur. J. 2014; 20: 14614
29 Cai S.-L, Zhang Y.-B, Pun AB, He B, Yang J, Toma FM, Sharp ID, Yaghi OM, Fan J, Zheng S.-R, Zhang W.-G, Liu Y. Chem. Sci. 2014; 5: 4693

30a Dong W.-l, Wang L, Ding H.-m, Zhao L, Wang D, Wang C, Wan L.-J. Langmuir 2015; 31: 11755
30b Dong W.-L, Li S.-Y, Yue J.-Y, Wang C, Wang D, Wan L.-J. Phys. Chem. Chem. Phys. 2016; 18: 17356

31 Li H, Chang J, Li S, Guan X, Li D, Li C, Tang L, Xue M, Yan Y, Valtchev V, Qiu S, Fang Q. J. Am. Chem. Soc. 2019; 141: 13324

32a Lu M, Liu J, Li Q, Zhang M, Liu M, Wang J.-L, Yuan D.-Q, Lan Y.-Q. Angew. Chem. Int. Ed. 2019; 58: 12392
32b Zhu H.-J, Lu M, Wang Y.-R, Yao S.-J, Zhang M, Kan Y.-H, Liu J, Chen Y, Li S.-L, Lan Y.-Q. Nat. Commun. 2020; 11: 497
32c Wu Q, Xie R.-K, Mao M.-J, Chai G.-L, Yi J.-D, Zhao S.-S, Huang Y.-B, Cao R. ACS Energy Lett. 2020; 5: 1005

33 Cai S, Sun B, Li X, Yan Y, Navarro A, Garzón-Ruiz A, Mao H, Chatterjee R, Yano J, Zhu C, Reimer JA, Zheng S, Fan J, Zhang W, Liu Y. ACS Appl. Mater. Interfaces 2020; 12: 19054
34 Zhang Y.-C, Zhou Y, Li Z.-T, Zhang D.-W. Tetrahedron 2015; 71: 605

35a Akiba K.-y, Ishikawa K, Inamoto N. Bull. Chem. Soc. Jpn. 1978; 51: 2674
35b Bryce MR, Moore AJ. Synth. Met. 1988; 25: 203
35c Bryce MR, Moore AJ, Hasan M, Ashwell GJ, Fraser AT, Clegg W, Hursthouse MB, Karaulov AI. Angew. Chem. Int. Ed. 1990; 29: 1450
35d Bryce MR, Finn T, Moore AJ, Batsanov AS, Howard JA. K. Eur. J. Org. Chem. 2000; 51
35e Jones AE, Christensen CA, Perepichka DF, Batsanov AS, Beeby A, Low PJ, Bryce MR, Parker AW. Chem. Eur. J. 2001; 7: 973
35f Barthelmes K, Sittig M, Winter A, Schubert US. Eur. J. Inorg. Chem. 2017; 3698
35g Hachem H, Vacher A, Dorcet V, Lorcy D. Organometallics 2017; 36: 2208

36a Martín N, Sańchez L, Herranz MÁ, Illescas B, Guldi DM. Acc. Chem. Res. 2007; 40: 1015
36b Wenger S, Bouit P.-A, Chen Q, Teuscher J, Di Censo D, Humphry-Baker R, Moser J.-E, Delgado JL, Martín N, Zakeeruddin SM, Grätzel M. J. Am. Chem. Soc. 2010; 132: 5164

37a Ogi D, Fujita Y, Kato M, Yamauchi T, Shirahata T, Yao M, Misaki Y. Eur. J. Org. Chem. 2019; 2725
37b Yamauchi T, Kato M, Shirahata T, Yao M, Misaki Y. Chem. Lett. 2019; 48: 1507

For other uses, see:

38a Hardouin-Lerouge M, Chesneau B, Allain M, Hudhomme P. J. Org. Chem. 2012; 77: 2441
38b Isla H, Gallego M, Pérez EM, Viruela R, Ortí E, Martín N. J. Am. Chem. Soc. 2010; 132: 1772

39 Bivaud S, Goeb S, Croué V, Dron PI, Allain M, Sallé M. J. Am. Chem. Soc. 2013; 135: 10018

40a Bivaud S, Goeb S, Croué V, Allain M, Pop F, Sallé M. Beilstein J. Org. Chem. 2015; 11: 966
40b Croué V, Goeb S, Szalóki G, Allain M, Sallé M. Angew. Chem. Int. Ed. 2016; 55: 1746
40c Szalóki G, Croué V, Allain M, Goeb S, Sallé M. Chem. Commun. 2016; 52: 10012
40d Szalóki G, Croué V, Carré V, Aubriet F, Alévêque O, Levillain E, Allain M, Aragó J, Ortí E, Goeb S, Sallé M. Angew. Chem. Int. Ed. 2017; 56: 16272
40e Colomban C, Szalóki G, Allain M, Gómez L, Goeb S, Sallé M, Costas M, Ribas X. Chem. Eur. J. 2017; 23: 3016
40f Szalóki G, Krykun S, Croué V, Allain M, Morille Y, Aubriet F, Carré V, Voitenko Z, Goeb S, Sallé M. Chem. Eur. J. 2018; 24: 11273

41 Yoshimura A, Henmi K, Kimura H, Sakakibara R, Ochi R, Shirahata T, Yorimitsu H, Misaki Y. Synthesis 2020; 52
42 Gordillo MA, Benavides PA, Panda DK, Saha S. ACS Appl. Mater. Interfaces 2020; 12: 12955
43 Yoshimura A, Kimura H, Kagawa K, Yoshioka M, Itou T, Vasu D, Shirahata T, Yorimitsu H, Misaki Y. Beilstein J. Org. Chem. 2020; 16: 974
44 Gholami M, Tykwinski RR. Chem. Rev. 2006; 106: 4997

45a Sugimoto T, Awaji H, Misaki Y, Yoshida Z, Kai Y, Nakagawa H, Kasai N. J. Am. Chem. Soc. 1985; 107: 5792
45b Sugimoto T, Misaki Y, Arai Y, Yamamoto Y, Yoshida Z, Kai Y, Kasai N. J. Am. Chem. Soc. 1988; 110: 628
45c Misaki Y, Matsumura Y, Sugimoto T, Yoshida Z.-i. Tetrahedron Lett. 1989; 30: 5289
45d Amaresh RR, Liu D, Konovalova T, Lakshmikantham MV, Cava MP, Kispert LD. J. Org. Chem. 2001; 66: 7757
45e Rajagopal D, Lakshmikantham MV, Cava MP. Org. Lett. 2002; 4: 2581
45f Coffin MA, Bryce MR, Batsanov AS, Howard JA. K. J. Chem. Soc., Chem. Commun. 1993; 552
45g Bryce MR, Coffin MA, Skabara PJ, Moore AJ, Batsanov AS, Howard JA. K. Chem. Eur. J. 2000; 6: 1955
45h Hasegawa M, Fujioka A, Kubo T, Honda T, Miyamoto H, Misaki Y. Chem. Lett. 2008; 37: 474
45i Horiuchi H, Misaki Y. Chem. Lett. 2010; 39: 989
45j Nishiwaki M, Tezuka M, Shirahata T, Misaki Y. Chem. Lett. 2011; 40: 467
45k Yamauchi T, Shibata Y, Aki T, Yoshimura A, Yao M, Misaki Y. Chem. Lett. 2018; 47: 1176

46 Shoji T, Araki T, Sugiyama S, Ohta A, Sekiguchi R, Ito S, Okujima T, Toyota K. J. Org. Chem. 2017; 82: 1657

47a Nelson JN, Krzyaniak MD, Horwitz NE, Rugg BK, Phelan BT, Wasielewski MR. J. Phys. Chem. A 2017; 121: 2241
47b Nelson JN, Zhang J, Zhou J, Rugg BK, Krzyaniak MD, Wasielewski MR. J. Phys. Chem. A 2018; 122: 9392

48 Hasegawa M, Endo J, Iwata S, Shimasaki T, Mazaki Y. Beilstein J. Org. Chem. 2015; 11: 972