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Synthesis 2024; 56(23): 3593-3614
DOI: 10.1055/a-2412-9407
DOI: 10.1055/a-2412-9407
paper
Application of C–H Functionalization in the Construction of Pyrene-Azobenzene Dyads
We thank Indian Institute of Science Education and Research Mohali (IISER Mohali) for funding this research work; S.S. thanks IISER Mohali for a PhD fellowship. We also thank the Departmental NMR facility supported by Department of Science and Technology, Ministry of Science and Technology, Fund for Improvement of S&T Infrastructure (DST-FIST; SR/FST/CS-II/2019/94 (TPN No. 32545)).
This paper is dedicated to the late Prof. Ramesh Kapoor (former faculty, IISER Mohali and Panjab University).
Abstract
Herein we report synthesis of pyrene-azobenzene dyads using the Pd(II)-catalyzed directing-group-assisted arylation of the ortho C(sp2)–H bond of pyrenecarboxamides as a key transformation. Many examples of directly connected pyrene-azobenzene dyads (without any linker) and glycine-based azobenzene-pyrene dyads have been synthesized. Initial incorporation of an acetanilide unit in the pyrene skeleton through Pd(II)-catalyzed directing-group-assisted ortho C(sp2)–H arylation by using iodoacetanilide was followed by the transformation of the acetanilide into an azobenzene unit to give the pyrene-azobenzene dyad. UV-Vis spectroscopic studies were performed to get the absorption properties (λmax (nm)) of all the compounds. Preliminary photoswitching studies in both forward and reverse directions and their related thermal reverse Z→E isomerization kinetics measurements were ascertained for representative compounds. Considering the importance of pyrene and azobenzene linked motifs as important chromophore-based photoswitchable molecules in chemical, materials, and supramolecular sciences research fields, this work enriches the library of pyrene-azobenzene dyads.
Key words
azobenzene - C–H functionalization - directing group - palladium - photoswitching - pyreneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2412-9407.
- Supporting Information
- CIF File
Publication History
Received: 02 June 2024
Accepted after revision: 10 September 2024
Accepted Manuscript online:
10 September 2024
Article published online:
14 October 2024
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References
- 1a Kakiuchi F, Murai S. Acc. Chem. Res. 2002; 35: 826
- 1b Rej S, Das A, Chatani N. Coord. Chem. Rev. 2021; 431: 213683
- 1c Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
- 1d Li B, Dixneuf PH. Chem. Soc. Rev. 2013; 42: 5744
- 1e Miura M, Satoh T, Hirano K. Bull. Chem. Soc. Jpn. 2014; 87: 751
- 1f Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
- 1g Lu M.-Z, Goh J, Maraswami M, Jia Z, Tian J.-S, Loh T.-P. Chem. Rev. 2022; 122: 17479
- 1h de Carvalho RL, Diogo EB. T, Homölle SL, Dana S, da Silva Júnior EN, Ackermann L. Chem. Soc. Rev. 2023; 52: 6359
- 1i Besset T, Poisson T, Pannecoucke X. Chem. Eur. J. 2014; 20: 16830
- 1j Chen X, Engle KM, Wang DH, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
- 1k Kuhl N, Hopkinson MN, Delord JW, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236
- 1l Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
- 1m Roger J, Gottumukkala AL, Doucet H. ChemCatChem 2010; 2: 20
- 1n Babu SA, Padmavathi R, Suwasia S, Dalal A, Bhattacharya D, Singh P, Tomar R. Stud. Nat. Prod. Chem. 2021; 71: 311
- 1o Yanagi T, Nogi K, Yorimitsu H. Tetrahedron Lett. 2018; 59: 2951
- 1p McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
- 1q Docherty JH, Lister TM, Mcarthur G, Findlay MT, Domingo-Legarda P, Kenyon J, Choudhary S, Larrosa I. Chem. Rev. 2023; 123: 7692
- 1r Sinha SK, Guin S, Maiti S, Biswas JP, Porey S, Maiti D. Chem. Rev. 2022; 122: 5682
- 1s Manoharan R, Jeganmohan M. Asian J. Org. Chem. 2019; 8: 1949
- 1t Banerjee A, Sarkar S, Patel BK. Org. Biomol. Chem. 2017; 15: 505
- 1u Mal A, Dana S, Choudhury D, Baidya M. Chem. Asian J. 2019; 14: 4074
- 1v Yang Y, Lan J, You J. Chem. Rev. 2017; 117: 8787
- 1w Babu SA, Padmavathi R, Aggarwal Y, Kaur R, Suwasia S. Pd-Catalyzed C(sp3)–H Activation by Native Directing Groups . In Handbook of CH-Functionalization . Maiti D. Wiley; Weinheim: 2022.
- 1x Dutta S, Bhattacharya T, Geffers FJ, Bürger M, Maiti D, Werz DB. Chem. Sci. 2022; 13: 2551
- 1y Zu B, Guo Y, Ke J, He C. Synthesis 2021; 53: 2029
- 1z Subramanian P, Rudolf GC, Kaliappan KP. Chem. Asian J. 2016; 11: 168
- 2a Rej S, Ano Y, Chatani N. Chem. Rev. 2020; 120: 1788
- 2b Daugulis O, Roane J, Tran LD. Acc. Chem. Res. 2015; 48: 1053
- 2c 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
- 2d He G, Wang B, Nack WA, Chen G. Acc. Chem. Res. 2016; 49: 635
- 2e Babu SA, Aggarwal Y, Patel P, Tomar R. Chem. Commun. 2022; 58: 2612
- 2f Li H, Li B.-J, Shi Z.-J. Catal. Sci. Technol. 2011; 1: 191
- 2g Rit RK, Yadav MR, Ghosh K, Sahoo AK. Tetrahedron 2015; 71: 4450
- 2h Zhang Q, Shi B.-F. Acc. Chem. Res. 2021; 54: 2750
- 2i Rouquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
- 2j Liu B, Romine AM, Rubel CZ, Engle KM, Shi B.-F. Chem. Rev. 2021; 121: 14957
- 2k Ni S.-F, Huang G, Chen Y, Wright JS, Li M, Dang L. Coord. Chem. Rev. 2022; 455: 214255
- 3a Shabashov D, Daugulis O. J. Am. Chem. Soc. 2010; 132: 3965
- 3b Nadres E, Santos GI. F, Shabashov D, Daugulis O. J. Org. Chem. 2013; 78: 9689
- 3c Kanyiva KS, Kuninobu Y, Kanai M. Org. Lett. 2014; 16: 1968
- 3d Seki A, Takahashi Y. Tetrahedron Lett. 2021; 74: 153130
- 3e Xu J, Qiao L, Shen J, Chai K, Shen C, Zhang P. Org. Lett. 2017; 19: 5661
- 3f Rej S, Chatani N. ACS Catal. 2018; 8: 6699
- 3g Parella R, Babu SA. J. Org. Chem. 2017; 82: 6550
- 3h Yu X, Yang F, Wu Y, Wu Y. Org. Lett. 2019; 21: 1726
- 3i Reddy C, Bisht N, Parella R, Babu SA. J. Org. Chem. 2016; 81: 12143
- 3j Padmavathi R, Sankar R, Gopalakrishnan B, Parella R, Babu SA. Eur. J. Org. Chem. 2015; 2015: 3727
- 3k Han J, Liu P, Wang C, Wang Q, Zhang J, Zhao Y, Shi D, Huang Z, Zhao Y. Org. Lett. 2014; 16: 5682
- 3l Huang L, Sun X, Li Q, Qi C. J. Org. Chem. 2014; 79: 6720
- 3m García-Rubia A, Laga E, Cativiela C, Urriolabeitia EP, Gomez-Arrayás R, Carretero JC. J. Org. Chem. 2015; 80: 3321
- 3n Andrade-Sampedro P, Matxain JM, Correa A. Chem. Eur. J. 2021; 27: 5782
- 4a Bolsakova J, Lukasevics L, Grigorjeva L. J. Org. Chem. 2020; 85: 4482
- 4b Martínez-Flores S, Mujica-Martinez CA, Polindara-García LA. Eur. J. Org. Chem. 2022; 2022: e202101517
- 4c Zhao Y, He G, Nack WA, Chen G. Org. Lett. 2012; 14: 2948
- 4d Kuai C, Wang L, Li B, Yang Z, Cui X. Org. Lett. 2017; 19: 2102
- 4e Aggarwal Y, Padmavathi R, Singh P, Babu SA. Asian J. Org. Chem. 2022; 11: e202200327
- 4f Bisht N, Singh P, Babu SA. Synthesis 2022; 54: 4059
- 4g Wang Z.-K, Wu Y.-J, Yao Q.-J, Shi B.-F. Angew. Chem. Int. Ed. 2023; 62: e202304706
- 4h Singh P, Babu SA, Aggarwal Y, Patel P. Asian J. Org. Chem. 2021; 10: 180
- 4i Landge GV, Midya SP, Rana J, Shinde DR, Balaraman E. Org. Lett. 2016; 18: 5252
- 4j Liu P, Han J, Chen CP, Shi DQ, Zhao YS. RSC Adv. 2015; 5: 28430
- 4k Bisht N, Babu SA, Tomar R. Asian J. Org. Chem. 2022; 11: e202200589
- 4l Wang X, Niu S, Xu L, Zhang C, Meng L, Zhang X, Ma D. Org. Lett. 2017; 19: 246
- 4m Singh P, Babu SA. Eur. J. Org. Chem. 2023; 26: e202300440
- 4n Narang U, Singh P, Babu SA. Eur. J. Org. Chem. 2023; 26: e202300463
- 4o Zeng W, Nukeyeva M, Wang Q, Jiang C. Org. Biomol. Chem. 2018; 16: 598
- 4p Tomar R, Kumar A, Dalal A, Bhattacharya D, Singh P, Babu SA. Asian J. Org. Chem. 2022; 11: e202200311
- 4q Andrade-Sampedro P, Matxain JM, Correa A. Chem. Eur. J. 2021; 27: 5782
- 5a Babu SA, Dalal A, Bodak S. Chemistry 2023; 5: 2713
- 5b Dalal A, Bodak S, Babu SA. Org. Biomol. Chem. 2024; 22: 1279
- 5c Odani R, Hirano K, Satoh T, Miura M. J. Org. Chem. 2013; 78: 11045
- 5d Just-Baringo X, Shin Y, Panigrahi A, Zarattini M, Nagyte V, Zhao L, Kostarelos K, Casiraghi C, Larrosa I. Chem. Sci. 2020; 11: 2472
- 5e Roy S, Pradhan S, Punniyamurthy T. Chem. Commun. 2018; 54: 3899
- 5f Iwasaki M, Kaneshika W, Tauchiya Y, Nakajima K, Nishihara Y. J. Org. Chem. 2014; 79: 11330
- 5g Ying J, Fu L.-Y, Zhong G, Wu X.-F. Org. Lett. 2019; 21: 5694
- 5h Gao Y, Zhang M, Wang C, Yang Z, Huang X, Feng R, Qi C. Chem. Commun. 2020; 56: 14231
- 5i Asako S, Ilies L, Nakamura E. J. Am. Chem. Soc. 2013; 135: 17755
- 5j Luo A, Zhang M, Fu Z, Lan J, Wu D, You J. Beilstein J. Org. Chem. 2020; 16: 530
- 5k Sire C, Cattey H, Tsivery A, Hierso J.-C, Roger J. Adv. Synth. Catal. 2022; 364: 440
- 5l Coventry DN, Batsanov AS, Goeta AE, Howard JA. K, Marder TB, Perutz RN. Chem. Commun. 2005; 2172
- 6a Nguyen TH. L, Gigant N, Joseph D. ACS Catal. 2018; 8: 1546
- 6b Mishra NK, Park J, Oh H, Han SH, Kim IS. Tetrahedron 2018; 74: 6769
- 6c Murahashi S. J. Am. Chem. Soc. 1955; 77: 6403
- 6d Murahashi S, Horiie S. J. Am. Chem. Soc. 1956; 78: 4816
- 6e Fahey DR. J. Organomet. Chem. 1971; 27: 283
- 6f Fahey DR. J. Chem. Soc. D 1970; 417a
- 6g Suwasia S, Venkataramani S, Babu SA. Org. Biomol. Chem. 2023; 21: 1793
- 6h Padmavathi R, Babu SA. Org. Biomol. Chem. 2023; 21: 2689
- 7a Babu SA, Kaur R, Singh H, Kumar A. Targets Heterocycl. Syst. 2023; 27: 378
- 7b Aihara Y, Wuelbern J, Chatani N. Bull. Chem. Soc. Jpn. 2015; 88: 438
- 7c Uemura T, Yamaguchi M, Chatani N. Angew. Chem. Int. Ed. 2016; 55: 3162
- 7d Kaur R, Singh H, Babu SA. Synthesis 2023; 55: 3535
- 7e Banga S, Babu SA. Eur. J. Org. Chem. 2024; 27: e202400272
- 8a Léonard E, Mangin F, Villette C, Billamboz M, Len C. Catal. Sci. Technol. 2016; 6: 379
- 8b Bandara HM. D, Burdette SC. Chem. Soc. Rev. 2012; 41: 1809
- 8c Beharry AA, Woolley GA. Chem. Soc. Rev. 2011; 40: 4422
- 8d Hamon F, Djedaini-Pilard F, Barbot F, Len C. Tetrahedron 2009; 65: 10105
- 8e Merino E. Chem. Soc. Rev. 2011; 40: 3835
- 8f Chang CY, Fedele C, Priimagi A, Shishido A, Barrett CJ. Adv. Optical Mater. 2019; 7: 1900091
- 8g Zhao M.-Y, Tang Y.-F, Han G.-Z. Molecules 2023; 28: 6741
- 8h Dong M, Babalhavaeji A, Samanta S, Beharry AA, Woolley GA. Acc. Chem. Res. 2015; 48: 2662
- 8i Xu W.-C, Sun S, Wu S. Angew. Chem. Int. Ed. 2019; 58: 9712
- 8j Chevalier A, Renard P.-Y, Romieu A. Chem. Asian J. 2017; 12: 2008
- 8k Amutha AS, Kumar KR. S, Tamaoki N. ChemPhotoChem 2019; 3: 337
- 8l Wagner-Wysiecka E, Łukasik N, Biernat JF, Luboch E. J. Inclusion Phenom. Macrocyclic Chem. 2018; 90: 189
- 8m Zhu M, Zhou H. Org. Biomol. Chem. 2018; 16: 8434
- 8n Crespi S, Simeth NA, König B. Nat. Rev. 2019; 3: 133
- 9a Westphal MV, Schafroth MA, Sarott RC, Imhof MA, Bold CP, Leippe P, Dhopeshwarkar A, Grandner JM, Katritch V, Mackie K, Trauner D, Carreira EM, Frank JA. J. Am. Chem. Soc. 2017; 139: 18206
- 9b Palasis KA, Lokman NA, Quirk BC, Adwal A, Scolaro L, Huang W, Ricciardelli C, Oehler MK, McLaughlin RA, Abell AD. Int. J. Mol. Sci. 2021; 22: 10844
- 9c Blanco B, Palasis KA, Adwal A, Callen DF, Abell AD. Bioorg. Med. Chem. 2017; 25: 5050
- 9d Thapaliya ER, Zhao J, Ellis-Davies GC. R. ACS Chem. Neurosci. 2019; 10: 2481
- 9e Verwilst P, Han J, Lee J, Mun S, Kang H.-G, Kim JS. Biomaterials 2017; 115: 104
- 9f Wegener M, Hansen MJ, Driessen AJ. M, Szymanski W, Feringa BL. J. Am. Chem. Soc. 2017; 139: 17979
- 9g Szymanski W, Ourailidou ME, Velema WA, Dekker FJ, Feringa BL. Chem. Eur. J. 2015; 21: 16517
- 10a Figueira-Duarte TM, Müllen K. Chem. Rev. 2011; 111: 7260
- 10b Bains G, Patel AB, Narayanaswami V. Molecules 2011; 16: 7909
- 10c Manandhar E, Wallace KJ. Inorg. Chim. Acta 2012; 381: 15
- 10d Hong Y, Lam JW. Y, Tang BZ. Chem. Soc. Rev. 2011; 40: 5361
- 10e Casas-Solvas JM, Howgego JD, Davis AP. Org. Biomol. Chem. 2014; 12: 212
- 10f Zych D. Molecules 2019; 24: 2551
- 10g Feng X, Hu J.-Y, Redshaw C, Yamato T. Chem. Eur. J. 2016; 22: 11898
- 10h Wu J, Zou Y, Li C, Sicking W, Piantanida I, Yi T, Schmuck C. J. Am. Chem. Soc. 2012; 134: 1958
- 10i Sato Y, Tanabe YT, Nishizawa S. Org. Biomol. Chem. 2020; 18: 4009
- 10j Astakhova IV, Korshun VA, Wengel J. Chem. Eur. J. 2008; 14: 11010
- 11 For a selected review on azobenzene-pyrene dyad: Porcu P, Estrada-Montaño AS, Vonlanthen M, Cuétara-Guadarrama F, González-Méndez I, Sorroza-Martínez K, Zaragoza-Galán G, Rivera E. Dyes Pigm. 2022; 197: 109858
- 12a Yamauchi M, Yokoyama K, Aratani N, Yamada H, Masuo S. Angew. Chem. Int. Ed. 2019; 58: 14173
- 12b Joo HN, Nguyen TV. T, Chae HK, Seo YJ. Bioorg. Med. Chem. Lett. 2017; 27: 2415
- 12c Nachtigall O, Lomoth R, Dahlstrand C, Lundstedt A, Gogoll A, Webb MJ, Grennberg H. Eur. J. Org. Chem. 2014; 2014: 966
- 12d El-Kadri OM, Tessema T.-D, Almotawa RM, Arvapally RK, Al-Sayah MH, Omary MA, El-Kaderi HM. ACS Omega 2018; 3: 15510
- 12e Thu P, Han M. Int. J. Mol. Sci. 2023; 24: 4504
- 12f Bluemmel P, Setaro A, Popeney CS, Haag R, Reich S. Phys. Status Solidi B 2010; 247: 2891
- 12g Joo HN, Le BH, Seo YJ. Tetrahedron Lett. 2017; 58: 679
- 12h Mohamed MG, Hsiao C.-H, Luo F, Daic L, Kuo S.-W. RSC Adv. 2015; 5: 45201
- 13 Synthesis of azobenzene-pyrene dyad via cross-coupling: Han M, Okui Y, Hirade T. J. Mater. Chem. C 2013; 1: 3448
- 14a Tomar R, Suwasia S, Choudhury AR, Venkataramani S, Babu SA. Chem. Commun. 2022; 58: 12967
- 14b Dalal A, Babu SA. Synthesis 2021; 53: 3307
- 15a Kumar P, Srivastava A, Sah C, Devi S, Venkataramani S. Chem. Eur. J. 2019; 25: 11924
- 15b Kumar P, Bala I, De R, Pal SK, Venkataramani S. Chem. Eur. J. 2023; 29: e202202876
- 15c Gupta D, Gaur AK, Kumar P, Kumar H, Mahadevan A, Devi S, Roy S, Venkataramani S. Chem. Eur. J. 2021; 27: 3463
- 16 Deposition number CCDC 2358212 (for 13k), contain supplementary crystallographic data for this paper. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
Selected reviews on C–H functionalization:
Selected reviews on bidentate directing-group-assisted C–H functionalization:
For selected reports on bidentate directing-group-assisted C(sp2)–H functionalization:
For selected reports on bidentate directing-group-assisted C(sp2)–H functionalization:
For selected reports on C(sp2)–H functionalization of pyrene:
For selected reports on C(sp2)–H functionalization, synthesis of functionalized azobenzenes:
Selected reviews dealing with azobenzenes:
For selected articles on azobenzene-pyrene dyad: