Rhodium-Catalyzed Stitching Reactions for the Facile Synthesis of Extended π-Conjugated Compounds

Abstract

π-Conjugated compounds have been extensively investigated as potentially useful organic materials, however, accessible structures are currently still limited, mainly due to the lack of efficient synthetic methods. In this regard, a new synthetic strategy termed the ‘stitching reaction’ has been recently devised that allows facile access to novel types of bridged π-conjugated compounds in a convergent manner under rhodium catalysis. In addition, this synthetic strategy has been successfully applied to the preparation of π-conjugated polymers that cannot be synthesized via existing methods. Herein an overview that includes the physical properties of newly synthesized π-conjugated compounds is provided.

1 Introduction

2 Synthesis of Novel Fused Oligosiloles by the Stitching Reaction and Their Properties

3 Synthesis of Hydrocarbon-Based Fused π-Conjugated Compounds by the Stitching Reaction

4 Synthesis of New π-Conjugated Polymers by Stitching Polymerization

5 Conclusion

Key words

alkynes - π-conjugated compounds - π-conjugated polymers - rhodium - silicon - stitching reaction - stitching polymerization

Publikationsverlauf

Eingereicht: 28. März 2022

Angenommen nach Revision: 19. April 2022

Accepted Manuscript online:
19. April 2022

Artikel online veröffentlicht:
31. Mai 2022

• References

• 1 Johnson WS. Acc. Chem. Res. 1968; 1: 1
• 2a Trost BM, Shi Y. J. Am. Chem. Soc. 1991; 113: 701
• 2b Trost BM, Shi Y. J. Am. Chem. Soc. 1993; 115: 9421
• 3 Koga Y, Kaneda T, Saito Y, Murakami K, Itami K. Science 2018; 359: 435
• 4a Fu H, Cheng Y. Curr. Org. Chem. 2012; 16: 1423
• 4b Ohshita J. Macromol. Chem. Phys. 2009; 210: 1360
• 4c Wong WW. H, Hooper JF, Holmes AB. Aust. J. Chem. 2009; 62: 393
• 4d Chen J, Cao Y. Macromol. Rapid Commun. 2007; 28: 1714
• 5a Yamaguchi S, Xu C, Tamao K. J. Am. Chem. Soc. 2003; 125: 13662
• 5b Yamada H, Xu C, Fukazawa A, Wakamiya A, Yamaguchi S. Macromol. Chem. Phys. 2009; 210: 904
• 6 Shintani R, Iino R, Nozaki K. J. Am. Chem. Soc. 2016; 138: 3635
• 7 Shintani R, Misawa N, Tsuda T, Iino R, Fujii M, Yamashita K, Nozaki K. J. Am. Chem. Soc. 2017; 139: 3861
• 8 Hamada N, Tsuda T, Shintani R. Eur. J. Org. Chem. 2021; 4824
• 9 Takano R, Shintani R, Fukazawa A, Yamaguchi S, Nakabayashi K, Ohkoshi S, Nozaki K. Organometallics 2017; 36: 2646
• 10 Lee SJ, Kim J, Tsuda T, Takano R, Shintani R, Nozaki K, Majima Y. Appl. Phys. Express 2019; 12: 125007
• 11a Halton B. Eur. J. Org. Chem. 2005; 3391
• 11b Bergmann ED. Chem. Rev. 1968; 68: 41
• 12a Rudebusch GE, Fix AG, Henthorn HA, Vonnegut CL, Zakharov LN, Haley MM. Chem. Sci. 2014; 5: 3627
• 12b Marshall JL, Rudebusch GE, Vonnegut CL, Zakharov LN, Haley MM. Tetrahedron Lett. 2015; 56: 3235
• 13 Shintani R, Kishikawa S, Nakamura K, Tsuda T, Nozaki K. Chem. Commun. 2019; 55: 1072
• 14a Dai G, Chang J, Shi X, Zhang W, Zheng B, Huang K.-W, Chi C. Chem. Eur. J. 2015; 21: 2019
• 14b Li C, Liu C, Li Y, Zhu X, Wang Z. Chem. Commun. 2015; 51: 693
• 14c Kawase T, Fujiwara T, Kitamura C, Konishi A, Hirao Y, Matsumoto K, Kurata H, Kubo T, Shinamura S, Mori H, Miyazaki E, Takimiya K. Angew. Chem. Int. Ed. 2010; 49: 7728
• 15a Kawase T, Nishida J. Chem. Rec. 2015; 15: 1045
• 15b Saito M. Symmetry 2010; 2: 950
• 16 Takahashi K, Ito S, Shintani R, Nozaki K. Chem. Sci. 2017; 8: 101
• 17 Zhou A.-H, Pan F, Zhu C, Ye L.-W. Chem. Eur. J. 2015; 21: 10278
• 18a Liu T.-P, Xing C.-H, Hu Q.-S. Angew. Chem. Int. Ed. 2010; 49: 2909
• 18b Kaiser RP, Hessler F, Mosinger J, Císařová I, Kotora M. Chem. Eur. J. 2015; 21: 13577
• 18c Gorin DJ, Watson ID. G, Toste FD. J. Am. Chem. Soc. 2008; 130: 3736
• 19 Nishida M, Shintani R. Chem. Eur. J. 2019; 25: 7475
• 20 Nishida M, Lee D, Shintani R. J. Org. Chem. 2020; 85: 8489
• 21a Tan NS. L, Lowe AB. Angew. Chem. Int. Ed. 2020; 59: 5008
• 21b Shiotsuki M, Sanda F, Masuda T. Polym. Chem. 2011; 2: 1044
• 22 Ikeda S, Shintani R. Angew. Chem. Int. Ed. 2019; 58: 5734
• 23 Kishimoto Y, Itou M, Miyatake T, Ikariya T, Noyori R. Macromolecules 1995; 28: 6662
• 24 Ikeda S, Hanamura Y, Tada H, Shintani R. J. Am. Chem. Soc. 2021; 143: 19559