Generic placeholder image

Letters in Organic Chemistry

Author(s): Faride Ranjbari, Salar Hemmati* and Mohammad Reza Rashidi

DOI: 10.2174/1570178617666200207102604

DownloadDownload PDF Flyer Cite As
Synthesis of (E)-1,2-Bis[4-[di(1H-pyrrol-2-yl)methyl]phenyl]ethene as a New Bis(dipyrromethane) Building Block

Page: [795 - 800] Pages: 6

  • * (Excluding Mailing and Handling)

Abstract

Dipyrromethanes are useful intermediates in the synthesis of porphyrins and their analogs. In this paper, we report the synthesis of a new bis(dipyrromethane) {(E)-1,2-bis[4-[di(1H-pyrrol-2- yl)methyl]phenyl]ethene}, from (E)-4,4'-1,2-ethenediylbis(benzaldehyde), showing a long resonance chain with improved UV spectrometric properties. This product has high potential in the synthesis of new bis(porphyrins) or other related compounds.

Keywords: Aldehydes, bis(dipyrromethanes), bis(porphyrins), dipyrromethanes, porphyrins, pyrrole.

Graphical Abstract

[1]
Gryko, D.T.; Gryko, D.; Lee, C-H. Chem. Soc. Rev., 2012, 41(10), 3780-3789.
[http://dx.doi.org/10.1039/c2cs00003b] [PMID: 22419038]
[2]
Pereira, N.A.M.; Pinho e Melo, T.M.V.D. Org. Prep. Proced. Int., 2014, 46, 183-213.
[http://dx.doi.org/10.1080/00304948.2014.903140]
[3]
Lopes, S.M.M.; Lemos, A.; Pinho e Melo, T.M.V.D. Eur. J. Org. Chem., 2014, 2014, 7039-7048.
[http://dx.doi.org/10.1002/ejoc.201402944]
[4]
Suzuki, M.; Osuka, A. Org. Lett., 2003, 5(21), 3943-3946.
[http://dx.doi.org/10.1021/ol035650x] [PMID: 14535749]
[5]
Wood, T.E.; Thompson, A. Chem. Rev., 2007, 107(5), 1831-1861.
[http://dx.doi.org/10.1021/cr050052c] [PMID: 17430001]
[6]
Lindsey, J.S. Acc. Chem. Res., 2010, 43(2), 300-311.
[http://dx.doi.org/10.1021/ar900212t] [PMID: 19863076]
[7]
Senge, M.O. Chem. Commun. (Camb.), 2011, 47(7), 1943-1960.
[http://dx.doi.org/10.1039/c0cc03984e] [PMID: 21218237]
[8]
Gryko, D.T.; Koszarna, B. Org. Biomol. Chem., 2003, 1(2), 350-357.
[http://dx.doi.org/10.1039/b208950e] [PMID: 12929430]
[9]
Beyzavi, M.H.; Lentz, D.; Reissig, H-U.; Wiehe, A. Chemistry, 2013, 19(20), 6203-6208.
[http://dx.doi.org/10.1002/chem.201300179] [PMID: 23520154]
[10]
Gale, P.A.; Anzenbacher, P., Jr; Sessler, J.L. Coord. Chem. Rev., 2001, 222, 57-102.
[http://dx.doi.org/10.1016/S0010-8545(01)00346-0]
[11]
Brückner, C.; Posakony, J.J.; Johnson, C.K.; Boyle, R.W.; James, B.R.; Dolphin, D. J. Porphyr. Phthalocyanines, 1998, 2, 455-465.
[http://dx.doi.org/10.1002/(SICI)1099-1409(199811/12)2:6<455:AID-JPP67>3.0.CO;2-C]
[12]
Lee, C-H.; Lindsey, J.S. Tetrahedron, 1994, 50, 11427-11440.
[http://dx.doi.org/10.1016/S0040-4020(01)89282-6]
[13]
Prathapan, S.; Johnson, T.E.; Lindsey, J.S. J. Am. Chem. Soc., 1993, 115, 7519-7520.
[http://dx.doi.org/10.1021/ja00069a068]
[14]
Lindsey, J.S.; Prathapan, S.; Johnson, T.E.; Wagner, R.W. Tetrahedron, 1994, 50, 8941-8968.
[http://dx.doi.org/10.1016/S0040-4020(01)85364-3]
[15]
Awuah, S.G.; You, Y. RSC Advances, 2012, 2, 11169-11183.
[http://dx.doi.org/10.1039/c2ra21404k]
[16]
Galangau, O.; Dumas-Verdes, C.; Méallet-Renault, R.; Clavier, G. Org. Biomol. Chem., 2010, 8(20), 4546-4553.
[http://dx.doi.org/10.1039/c004812g] [PMID: 20714498]
[17]
Josefsen, L.B.; Boyle, R.W. Theranostics, 2012, 2(9), 916-966.
[http://dx.doi.org/10.7150/thno.4571] [PMID: 23082103]
[18]
Kursunlu, A.N.; Guler, E.; Ucan, H.I.; Boyle, R.W. Dyes Pigm., 2012, 94, 496-502.
[http://dx.doi.org/10.1016/j.dyepig.2012.02.006]
[19]
Olivier, J-H.; Haefele, A.; Retailleau, P.; Ziessel, R. Org. Lett., 2010, 12(3), 408-411.
[http://dx.doi.org/10.1021/ol902386u] [PMID: 20038132]
[20]
Nepomnyashchii, A.B.; Cho, S.; Rossky, P.J.; Bard, A.J. J. Am. Chem. Soc., 2010, 132(49), 17550-17559.
[http://dx.doi.org/10.1021/ja108108d] [PMID: 21090724]
[21]
Ulrich, G.; Ziessel, R.; Harriman, A. Angew. Chem. Int. Ed., 2008, 47, 1184-1201.
[http://dx.doi.org/10.1002/anie.200702070]
[22]
Ulrich, G.; Ziessel, R.; Harriman, A. Angew. Chem., 2008, 120, 1202-1219.
[http://dx.doi.org/10.1002/ange.200702070]
[23]
Boens, N.; Leen, V.; Dehaen, W. Chem. Soc. Rev., 2012, 41(3), 1130-1172.
[http://dx.doi.org/10.1039/C1CS15132K] [PMID: 21796324]
[24]
Beyzavi, M.H.; Lentz, D.; Reissig, H-U.; Wiehe, A. Eur. J. Org. Chem., 2013, 2013, 269-282.
[http://dx.doi.org/10.1002/ejoc.201201295]
[25]
Dudic, M.; Lhota’k, P.; Kra’l, V.; Lang, K.; Stibor, I. Tetrahedron Lett., 1999, 40, 5949-5952.
[26]
Laha, J.K.; Dhanalekshmi, S.; Taniguchi, M.; Ambroise, A.; Lindsey, J.S. Org. Process Res. Dev., 2003, 7, 799-812.
[http://dx.doi.org/10.1021/op034083q]
[27]
Gowri Sreedevi, K.C.; Thomas, A.P.; Salini, P.S.; Ramakrishnan, S.; Anju, K.S.; Derry Holaday, M.G.; Reddy, M.L.P.; Suresh, C.H.; Srinivasan, A. Tetrahedron Lett., 2011, 52, 5995-5999.
[http://dx.doi.org/10.1016/j.tetlet.2011.08.163]
[28]
Tsuchimoto, T.; Hatanaka, K.; Shirakawa, E.; Kawakami, Y. Chem. Commun. (Camb.), 2003, 19, 2454-2455.
[http://dx.doi.org/10.1039/b308319e] [PMID: 14587728]
[29]
Sessler, J.L.; Hugdahl, J.; Johnson, M.R. J. Org. Chem., 1986, 51, 2838-2840.
[http://dx.doi.org/10.1021/jo00364a050]
[30]
Heiler, D.; McLendon, G.; Rogalskyj, P. J. Am. Chem. Soc., 1987, 109, 604-606.
[http://dx.doi.org/10.1021/ja00236a061]
[31]
Osuka, A.; Maruyama, K.; Yamazaki, I.; Tamai, N. J. Chem. Soc. Chem. Commun., 1988, 1243-1245.
[http://dx.doi.org/10.1039/c39880001243]
[32]
Zhao, H.; Liao, J.; Ning, J.; Xie, Y.; Cao, Y.; Chen, L.; Yang, D.; Wang, B. Adv. Synth. Catal., 2010, 352, 3083-3088.
[http://dx.doi.org/10.1002/adsc.201000336]
[33]
Guo, C.; Sun, S.; He, Q.; Lynch, V.M.; Sessler, J.L. Org. Lett., 2018, 20(17), 5414-5417.
[http://dx.doi.org/10.1021/acs.orglett.8b02322] [PMID: 30136850]
[34]
Madhu, S.; Ravikanth, M. Inorg. Chem., 2012, 51(7), 4285-4292.
[http://dx.doi.org/10.1021/ic202758r] [PMID: 22432414]
[35]
Zaidi, S.H.H.; Fico, R.M., Jr; Lindsey, J.S. Org. Process Res. Dev., 2006, 10, 118-134.
[http://dx.doi.org/10.1021/op050193g]
[36]
Gryko, D.T.; Clausen, C.; Lindsey, J.S. J. Org. Chem., 1999, 64, 8635-8647.
[http://dx.doi.org/10.1021/jo9911084]
[37]
Paolesse, R.; Pandey, R.K.; Forsyth, T.P.; Jaquinod, L.; Gerzevske, K.R.; Nurco, D.J.; Senge, M.O.; Licoccia, S.; Boschi, T.; Smith, K.M. J. Am. Chem. Soc., 1996, 118, 3869-3882.
[http://dx.doi.org/10.1021/ja9541138]
[38]
Bance, S.; Barber, H.J.; Woolman, A.M. J. Chem. Soc., 1943, 1-4.
[http://dx.doi.org/10.1039/JR9430000001]
[39]
Mata, J.A.; Falomir, E.; Llusar, R.; Peris, E. J. Organomet. Chem., 2000, 616, 80-88.
[http://dx.doi.org/10.1016/S0022-328X(00)00557-X]
[40]
Pye, C.; Fronczek, F.R.; Isovitsch, R. Helv. Chim. Acta, 2010, 93, 1162-1171.
[http://dx.doi.org/10.1002/hlca.200900343]
[41]
Madhu, S.; Rao, M.R.; Shaikh, M.S.; Ravikanth, M. Inorg. Chem., 2011, 50(10), 4392-4400.
[http://dx.doi.org/10.1021/ic102499h] [PMID: 21510624]