Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00032269.xml
CC BY-NC-ND 4.0 · SynOpen 2020; 04(02): 44-50
DOI: 10.1055/s-0040-1707429
DOI: 10.1055/s-0040-1707429
paper
A Modified Vilsmeier–Haack Strategy to Construct β-Pyridine-Fused 5,10,15,20-Tetraarylporphyrins
The authors are grateful to the University of Delhi for providing a DST PURSE grant. P.S. is grateful to UGC, New Delhi, India for the award of a Senior Research Fellowship.Further Information
Publication History
Received: 31 March 2020
Accepted after revision: 06 May 2020
Publication Date:
08 June 2020 (online)
Abstract
A modified Vilsmeier–Haack strategy has been developed to construct a novel series of π-extended nickel(II) or copper(II) complexes of 2-chloro-3-formyl- and 3-formylpyrido[2,3-b]porphyrins from 2-acetamido-meso-tetraarylporphyrins. After chromatographic purification and spectral characterization, nickel(II) complexes of 2-chloro-3-formyl- and 3-formylpyrido[2,3-b]porphyrins underwent reaction with malononitrile under Knoevenagel conditions to afford new porphyrins with extended π-conjugation in appreciable yields. On photophysical investigation, the newly prepared pyridoporphyrins displayed a significant redshift in their electronic absorption spectra as compared to simple meso-tetraarylporphyrin precursors.
Key words
2-chloro-3-formylpyrido[2,3-b]porphyrins - 3-formylpyrido[2,3-b]porphyrins - Knoevenagel condensation - redshift - synthesis - Vilsmeier–Haack reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707519.
- Supporting Information
-
References
- 1 Barber J. Chem. Soc. Rev. 2009; 38: 185
- 2 Denisov IG, Makris TM, Sligar SG. Chem. Rev. 2005; 105: 2253
- 3 Gust D, Moore TA, Moore AL. Acc. Chem. Res. 2001; 34: 40
- 4 Imahori H. J. Phys. Chem. B 2004; 108: 6130
- 5 Chen Y.-C, Hsu C.-Y, Lin RY. Y, Ho K.-C, Lin JT. ChemSusChem 2013; 6: 20
- 6 Ichiki T, Matsuo Y, Nakamura E. Chem. Commun. 2013; 49: 279
- 7 Humphrey JL, Kuciauskas D. J. Am. Chem. Soc. 2006; 128: 3902
- 8 Gautam P, Dhokale B, Shukla V, Singh CP, Bindra KS, Misra R. J. Photochem. Photobiol., A 2012; 239: 24
- 9 Linke-Schaetzel M, Anson CE, Powell AK, Buth G, Palomares E, Durrant JD, Balaban TS, Lehn J.-M. Chem. Eur. J. 2006; 12: 1931
- 10 Liu Z, Yasseri AA, Lindsey JS, Bocian DF. Science 2003; 302: 1543
- 11 Martin RE, Diederisch F. Angew. Chem. Int. Ed. 1999; 38: 1350
- 12 Conklin D, Nanayakkara S, Park T.-H, Lagadec MF, Stecher JT, Chen X, Therien MJ, Bonnell DA. ACS Nano 2013; 7: 4479
- 13 Sharma GD, Angaridis PA, Pipou S, Zervaki GE, Nikolaou V, Misra R, Coutsolelos AG. Org. Electron. 2015; 25: 295
- 14 Li L.-L, Diau EW. G. Chem. Soc. Rev. 2013; 42: 291
- 15 Balaban TS. Acc. Chem. Res. 2005; 38: 612
- 16 AbdulAlmohsin S, Cui JB. J. Phys. Chem. C 2012; 116: 9433
- 17 Mozer AJ, Griffith MJ, Tsekouras G, Wagner P, Wallace GG, Mori S, Sunahara K, Miyashita M, Earles JC, Gordon KC, Du L, Katoh R, Furube A, Officer DL. J. Am. Chem. Soc. 2009; 131: 15621
- 18 Borek C, Hanson K, Djurovich PI, Thompson ME, Aznavour K, Bau R, Sun Y, Forrest SR, Brooks J, Michalski L, Brown J. Angew. Chem. Int. Ed. 2007; 46: 1109
- 19 Graham KR, Yang Y, Sommer JR, Shelton AH, Schanze KS, Xue J, Reynolds JR. Chem. Mater. 2011; 23: 5305
- 20 Tu W, Lei J, Wang P, Ju H. Chem. Eur. J. 2011; 17: 9440
- 21 Wang Q, Lei J, Deng S, Zhang L, Ju H. Chem. Commun. 2013; 49: 916
- 22 Lavova L, Natale CD, Paolesse R. Sens. Actuators, B 2013; 179: 21
- 23 Gupta I, Fröhlich R, Ravikanth M. Eur. J. Org. Chem. 2008; 1884
- 24a Jaquinod L, Gros C, Olmstead MM, Antolovich M, Smith KM. Chem. Commun. 1996; 1475
- 24b Gros CP, Jaquinod L, Khoury RG, Olmstead MM, Smith KM. J. Porphyrins Phthalocyanines 1997; 1: 201
- 24c Silva AM. G, Faustino MA. F, Tome AC, Neves MG. P. M. S, Silva AM. S, Cavaleiro JA. S. J. Chem. Soc., Perkin Trans. 1 1999; 2752
- 24d Alonso CM. A, Neves MG. P. M. S, Tome AC, Silva AM. S, Cavaleiro JA. S. Tetrahedron 2005; 61: 11866
- 25 Silva AM. G, Tome AC, Neves MG. P. M. S, Cavaleiro JA. S. Synlett 2002; 7: 1155
- 26 Lacerda PS. S, Silva AM. G, Tome AC, Neves MG. P. M. S, Silva AM. S, Cavaleiro JA. S, Llamas-Saiz AL. Angew. Chem. Int. Ed. 2006; 45: 5487
- 27 Crossley MJ, McDonald JA. J. Chem. Soc., Perkin Trans. 1 1999; 2429
- 28 Tan K, Jaquinod L, Paolesse R, Nardis S, Natale CD, Carlo AD, Prodi L, Montalti M, Zaccheronie N, Smith KM. Tetrahedron 2004; 60: 1099
- 29 Singh DK, Nath M. Org. Biomol. Chem. 2015; 13: 1836
- 30 Alonso CM. A, Neves MG. P. M. S, Tome AC, Silva AM. S, Cavaleiro JA. S. Tetrahedron Lett. 2001; 42: 8307
- 31 Alonso CM. A, Neves MG. P. M. S, Tome AC, Silva AM. S, Cavaleiro JA. S. Eur. J. Org. Chem. 2004; 3233
- 32 Alonso CM. A, Serra VI. V, Neves MG. P. M. S, Tome AC, Silva AM. S, Paz FA. A, Cavaleiro JA. S. Org. Lett. 2007; 9: 2305
- 33 Tekuri CS, Singh P, Nath M. Org. Biomol. Chem. 2020; 18: 2516
- 34 Sharma S, Nath M. New J. Chem. 2011; 35, 1630
- 35 Tiwari R, Nath M. Dyes Pigm. 2018; 152: 161
- 36 Tiwari R, Nath M. SynOpen 2018; 2: 133
- 37a Ponomarev GV. Chem. Heterocycl. Compd. 1994; 30: 1444
- 37b Bonfantini EE, Burrell AK, Campbell WM, Crossley MJ, Gosper JJ, Harding MM, Officer DL, Reid DC. W. J. Porphyrins Phthalocyanines 2002; 6: 708
- 37c Moura NM. M, Faustino MA. F, Neves MG. P. M. S, Durate AC, Cavaleiro JA. S. J. Porphyrins Phthalocyanines 2011; 15: 652
- 37d Vicente MG. H, Smith KM. J. Org. Chem. 1991; 56: 4407
- 38a Meth-Cohn O, Narine B. Tetrahedron Lett. 1978; 2045
- 38b Meth-Cohn O, Narine B, Tarnowski B. Tetrahedron Lett. 1979; 3111
- 38c Meth-Cohn O, Narine B, Tarnowski B. J. Chem. Soc., Perkin Trans. 1 1981; 1520
- 38d Meth-Cohn O, Tarnowski B. Adv. Heterocycl. Chem. 1982; 31: 207
- 38e Deshpande MN, Seshadri S. Indian J. Chem. 1973; 11: 538
- 38f Marson CM. Tetrahedron 1992; 48: 3659
- 38g Venkanna P, Ranjana KC, Kumar MS, Ansari MB, Ali MA. Tetrahedron Lett. 2015; 56: 5164
- 38h Chupp JP, Metz SJ. J. Heterocycl. Chem. 1979; 16: 65