Abstract
The incorporation of a meta-phenylene moiety into a β-alkylated or meso-tetraarylporphyrin framework resulted in the formation of m-benziporphyrins. Their molecular design preserves all the essential virtues of the original tetrapyrrolic architecture of regular porphyrin, including the perfect match between the ionic radii of the inserted metal cation and the size of the macrocyclic (CNNN) core, and steric protection provided by thoughtfully chosen β-alkyl or meso-aryl substituents. The analogous incorporation of a pyridine moiety yielded a class of pyriporphyrins. The organometallic derivatives of m-benziporphyrins and pyriporphyrins are reminiscent of the large family of pincer ligand complexes, in which the metal–arene bond is supported by two amine or phosphine arms. This chapter relates the chemistry of the pincer ligand and that of the m-benziporphyrin (aza-m-benziporphyrin) emphasizing the fact that both groups have been structurally and functionally based on common dominators, i.e., on m-phenylene (aza-m-phenylene) rings.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Berlin K, Breitmaier E (1994) Angew Chem Int Ed Engl 33:1246
Stępień M, Latos-Grażyński L (2001) Chem A Eur J 7:5113
Stępień M, Latos-Grażyński L (2009) Aromaticity and tautomerism in porphyrins and porphyrinoids. In: Krygowski TM (ed) Aromaticity in heterocyclic compounds. Springer, Berlin, p 83. Chap 3
Pawlicki M, Latos-Grażyński L (2010) Carbaporphyrinoids – synthesis and coordination properties. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science: with applications to chemistry, physics, materials science, engineering, biology and medicine. World Scientific Publishing, Singapore, p 104. Chap 8
Stępień M, Latos-Grażyński L (2005) Acc Chem Res 38:88
Latos-Grażyński L, Rachlewicz K, Wojaczyński J (1999) Coord Chem Rev 190–192:109
Lash TD (2015) Org Biomol Chem 13:7846
Lash TD (2014) Chem Asian J 9:682
Lash TD (2017) Chem Rev 117:2313
Berlicka A, Latos-Grażyński L (2020) J Porphyrins Phtalocyanines 24:1
Lee CH, Roznyatovskiy V, Hong SJ, Sessler JL (2011) Porphyrins and porphyrin analogs bearing double bonds at one or more meso-positions. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science: with applications to chemistry, physics, materials science, engineering, biology and medicine. World Scientific Publishing, Singapore, p 197. Chap 13
Chmielewski PJ, Latos-Grażyński L, Rachlewicz K, Głowiak T (1994) Angew Chem Int Ed Engl 33:779
Furuta H, Asano T, Ogawa T (1994) J Am Chem Soc 116:767
Garbicz M, Latos-Grażyński L (2019) Angew Chem Int Ed 58:6089
Stępień M, Latos-Grażyński L (2002) J Am Chem Soc 124:3838
Stępień M, Latos-Grażyński L, Szterenberg L, Panek J, Latajka Z (2004) J Am Chem Soc 126:4566
Szyszko B, Latos-Grażyński L, Szterenberg L (2011) Angew Chem Int Ed 50:6587
Idec A, Szterenberg L, Latos-Grażyński L (2015) Chem A Eur J 21:12481
Idec A, Skonieczny J, Latos-Grażyński L, Pawlicki M (2016) Eur J Org Chem 2016:3691
Idec A, Pawlicki M, Latos-Grażyński L (2019) Chem A Eur J 25:200
Myśliborski R, Latos-Grażyński L (2005) Eur J Org Chem:5039
Myśliborski R, Latos-Grażyński L, Szterenberg L (2006) Eur J Org Chem:3064
Hurej K, Pawlicki M, Szterenberg L, Latos-Grażyński L (2016) Angew Chem Int Ed 55:1427
Hurej K, Pawlicki M, Latos-Grażyński L (2017) Chem A Eur J 23:2059
Hurej K, Pawlicki M, Latos-Grażyński L (2018) Chem A Eur J 23:115
Hung CH, Chang FC, Lin CY, Rachlewicz K, Stępień M, Latos-Grażyński L, Lee GH, Peng SM (2004) Inorg Chem 43:4118
Casitas A, Canta M, Sola M, Costas M, Ribas X (2011) J Am Chem Soc 133:19386
Bergbreiter DE, Osburn PL, Liu YS (1999) J Am Chem Soc 121:9531
Kraatz HB, Milstein D (1995) J Organomet Chem 488:223
Canty AJ, Minchin NJ, Skelton BW, White AH (1987) J Chem Soc Dalton Trans:1477
Albrecht M, van Koten G (2001) Angew Chem Int Ed 40:3750
van der Boom ME, Milstein D (2003) Chem Rev 103:1759
Benito-Garagorri D, Kirchner K (2008) Acc Chem Res 41:201
Whited MT, Grubbs RH (2009) Acc Chem Res 42:1607
Choi J, MacArthur AH, Brookhart M, Goldman AS (2011) Chem Rev 111:1761
Gunanathan C, Milstein D (2011) Acc Chem Res 44:588
van Koten G, Gebbink R (2011) Dalton Trans 40:8731
van Koten G (2013) The Monoanionic ECE-pincer ligand: a versatile privileged ligand platform-general considerations. Topics in organometallic chemistry. Springer, Cham, p 1
Lawrence MAW, Green KA, Nelson PN, Lorraine SC (2018) Polyhedron 143:11
Gorgas N, Kirchner K (2018) Acc Chem Res 51:1558
van Koten G (2019) NCN-pincer organometallics in bioorganometallic chemistry. Advances in bioorganometallic chemistry. Elsevier, Amsterdam, p 113. Chap 6
Valdes H, Rufino-Felipe E, Morales-Morales D (2019) J Organomet Chem:898
Alig L, Fritz M, Schneider S (2019) Chem Rev 119:2681
Haque A, Xu LL, Al-Balushi RA, Al-Suti MK, Ilmi R, Guo ZL, Khan MS, Wong WY, Raithby PR (2019) Chem Soc Rev 48:5547
Li J, Siegler M, Lutz M, Spek AL, Gebbink RJ, van Koten G (2010) Adv Synth Catal 352:2474
Bonnet S, van Lenthe JH, van Dam HJ, van Koten G, Gebbink RJ (2011) Dalton Trans 40:2542
Gagliardo M, Snelders DJ, Chase PA, Gebbink RJ, van Klink GR, van Koten G (2007) Angew Chem Int Ed 46:8558
Kohl SW, Weiner L, Schwartsburd L, Konstantinovski L, Shimon LJ, Ben-David Y, Iron MA, Milstein D (2009) Science 324:74
Kickham JE, Loeb SJ (1995) Inorg Chem 34:5656
Font M, Ribas X (2016) Pincerlike cyclic systems for unraveling fundamental coinage metal redox processes. Topics in organometallic chemistry. Springer, Cham, p 269
Casitas A, King AE, Parella T, Costas M, Stahl SS, Ribas X (2010) Chem Sci 1:326
Ribas X, Calle C, Poater A, Casitas A, Gomez L, Xifra R, Parella T, Benet-Buchholz J, Schweiger A, Mitrikas G, Sola M, Llobet A, Stack T (2010) J Am Chem Soc 132:12299
Lash TD, Chaney ST, Richter DT (1998) J Org Chem 63:9076
Darrow WT, Lash TD (2017) J Porphyrins Phtalocyanines 21:532
Lash TD, Yant VR (2009) Tetrahedron 65:9527
Stępień M, Latos-Grażyński L, Szterenberg L (2004) Inorg Chem 43:6654
Lash TD, Toney AM, Castans KM, Ferrence GM (2013) J Org Chem 78:9143
Fosu SC, Ferrence GM, Lash TD (2014) J Org Chem 79:11061
Hung CH, Chang GF, Kumar A, Lin GF, Luo LY, Ching WM, Diau EWG (2008) Chem Commun:978
Chang GF, Kumar A, Ching WM, Chu HW, Hung CH (2009) Chem Asian J 4:164
Chang GF, Wang CH, Lu HC, Kan LS, Chao I, Chen WH, Kumar A, Lo LY, dela Rosa MAC, Hung CH (2011) Chem A Eur J 17:11332
Huang CS, Li YL, Yang JE, Cheng N, Liu HB, Li YJ (2010) Chem Commun 46:3161
Singh K, Abebayehu A, Mulugeta E, Sareen D, Lee CH (2016) J Porphyr Phthalocyanines 20:21
Jeong SD, Nowak-Krol A, Kim Y, Kim SJ, Gryko DT, Lee CH (2010) Chem Commun 46:8737
Park D, Jeong SD, Ishida M, Lee CH (2014) Chem Commun 50:9277
Abebayehu A, Park D, Hwang S, Dutta R, Lee CH (2016) Dalton Trans 45:3093
Jeong SD, Hong SJ, Park KJ, Ham S, Sessler JL, Lynch V, Lee CH (2007) J Org Chem 72:6232
Brückner C, Akhigbe J, Samankumara LP (2014) Porphyrin analogs containing non-pyrrolic heterocycles. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science: with applications to chemistry, physics, materials science, engineering, biology and medicine. World Scientific Publishing, Singapore, p 4. Chap 164
Lash TD, Pokharel K, Serling JM, Yant VR, Ferrence GM (2007) Org Lett 9:2863
Berlin K, Breitmaier E (1994) Angew Chem Int Ed Engl 33:219
Sim EK, Jeong SD, Yoon DW, Hong SJ, Kang Y, Lee CH (2006) Org Lett 8:3355
Szyszko B, Latos-Grażyński L (2015) Chem Soc Rev 44:3588
Stępień M, Latos-Grażyński L (2003) Org Lett 5:3379
Stępień M, Latos-Grażyński L (2003) Inorg Chem 42:6183
Stępień M, Latos-Grażyński L, Szterenberg L (2007) J Org Chem 72:2259
El-Beck JA, Lash TD (2006) Org Lett 8:5263
Lash TD (1995) Angew Chem Int Ed Engl 34:2533
Richter DT, Lash TD (2001) Tetrahedron 57:3657
Stępień M, Latos-Grażyński L, Lash TD, Szterenberg L (2001) Inorg Chem 40:6892
Lash TD, Szymanski JT, Ferrence GM (2007) J Org Chem 72:6481
Szymanski JT, Lash TD (2003) Tetrahedron Lett 44:8613
Ryppa C, Niedzwiedzki D, Morozowich NL, Srikanth R, Zeller M, Frank HA, Bruckner C (2009) Chem A Eur J 15:5749
Kozyrev AN, Alderfer JL, Dougherty TJ, Pandey RK (1999) Angew Chem Int Ed 38:126
Toganoh M, Furuta H (2010) Synthesis and metal coordination of N-confused and N-fused porphyrinoids. In: Kadish KM, Smith KM, Guilard R (eds) Handbook of porphyrin science: with applications to chemistry, physics, materials science, engineering, biology and medicine. World Scientific Publishing, Singapore, p 295. Chap 8
Chmielewski PJ, Latos-Grażyński L (2005) Coord Chem Rev 249:2510
Pacholska-Dudziak E, Latos-Grażyński L (2007) Eur J Inorg Chem:2594
Ishizuka T, Ikeda S, Toganoh M, Yoshida I, Ishikawa Y, Osuka A, Furuta H (2008) Tetrahedron 64:4037
Toganoh M, Furuta H (2012) Chem Commun 48:937
Myśliborski R, Rachlewicz K, Latos-Grażyński L (2007) J Porphyrins Phtalocyanines 11:172
Lash TD, Young AM, Rasmussen JM, Ferrence GM (2011) J Org Chem 76:5636
Lash TD, Rasmussen JM, Bergman KM, Colby DA (2004) Org Lett 6:549
Adams KR, Bonnett R, Burke PJ, Salgado A, Valles MA (1993) J Chem Soc Chem Commun:1860
Adams KR, Bonnett R, Burke PJ, Salgado A, Valles MA (1997) J Chem Soc Perkin Trans:11769
Myśliborski R, Rachlewicz K, Latos-Grażyński L (2006) Inorg Chem 45:7828
Ellis D, McKay D, Macgregor SA, Rosair GM, Welch AJ (2010) Angew Chem Int Ed 49:4943
Kaplan L, Wendling LA, Wilzbach KE (1971) J Am Chem Soc 93:3819
Krempner C, Reinke H, Wustrack R (2007) Inorg Chem Comm 10:239
Pope RM, VanOrden SL, Cooper BT, Buckner SW (1992) Organometallics 11:2001
Sattler A, Parkin G (2009) Nature 463:523
Hu S, Shima T, Hou Z (2014) Nature 512:413
Kvaskoff D, Lueerssen H, Bednarek P, Wentrup C (2014) J Am Chem Soc 136:15203
Jakoobi M, Sergeev AG (2019) Chem Asian J 14:2181
Hicks J, Vasko P, Goicoechea JM, Aldridge S (2019) J Am Chem Soc 141:11000
Zhang XX, Parks GF, Wayland BB (1997) J Am Chem Soc 119:7938
Hurej K (2017) PhD thesis, University of Wrocław
Frech CM, Shimon LJ, Milstein D (2007) Chem A Eur J 13:7501
Frech CM, Milstein D (2006) J Am Chem Soc 128:12434
Gandelman M, Konstantinovski L, Rozenberg H, Milstein D (2003) Chem A Eur J 9:2595
Vigalok A, Rybtchinski B, Shimon LJW, Ben-David Y, Milstein D (1999) Organometallics 18:895
Chevrier B, Weiss R, Chottard JC, Lange M, Mansuy D (1981) J Am Chem Soc 103:2899
Szyszko B, Kupietz K, Szterenberg L, Latos-Grażyński L (2014) Chem A Eur J 20:1376
Stępień M, Latos-Grażyński L, Sprutta N, Chwalisz P, Szterenberg L (2007) Angew Chem Int Ed 46:7869
Stępień M, Szyszko B, Latos-Grażyński L (2010) J Am Chem Soc 132:3140
Grzegorzek N, Pawlicki M, Szterenberg L, Latos-Grażyński L (2009) J Am Chem Soc 131:7224
Pawlicki M, Kańska I, Latos-Grażyński L (2007) Inorg Chem 46:6575
Stępień M, Sprutta N, Latos-Grażyński L (2011) Angew Chem Int Ed 50:4288
Singh R, Mukherjee A (2019) ACS Catal 9:3604
Che CM, Lo VKY, Zhou CY, Huang JS (2011) Chem Soc Rev 40:1950
Niino T, Toganoh M, Andrioletti B, Furuta H (2006) Chem Commun:4335
Fields KB, Engle JT, Sripothongnak S, Kim C, Zhang XP, Ziegler CJ (2011) Chem Commun 47:749
Rachlewicz K, Wang SL, Ko JL, Hung CH, Latos-Grażyński L (2004) J Am Chem Soc 126:4420
Pawlicki M, Latos-Grażyński L (2005) J Org Chem 70:9123
Chmielewski MJ, Pawlicki M, Sprutta N, Szterenberg L, Latos-Grażyński L (2006) Inorg Chem 45:8664
Pacholska-Dudziak E, Skonieczny J, Pawlicki M, Szterenberg L, Ciunik Z, Latos-Grażyński L (2008) J Am Chem Soc 130:6182
Idec A, Pawlicki M, Latos-Grażyński L (2017) Inorg Chem 56:10337
Grzegorzek N, Nojman E, Szterenberg L, Latos-Grażyński L (2013) Inorg Chem 52:2599
Grocka I, Latos-Grażyński L, Stępień M (2013) Angew Chem Int Ed 52:1044
Białek MJ, Chmielewski PJ, Latos-Grażyński L (2019) Chem A Eur J 25:14536
Lash TD, Colby DA, Szczepura LF (2004) Inorg Chem 43:5258
Szyszko B, Latos-Grażyński L (2011) Organometallics 30:4354
Szyszko B, Latos-Grażyński L, Szterenberg L (2012) Chem Commun 48:5004
Gao RX, AbuSalim DI, Lash TD (2017) J Org Chem 82:6680
Szyszko B, Szterenberg L, Białońska A, Latos-Grażyński L (2015) Angew Chem Int Ed 54:4932
Myśliborski R, Latos-Grażyński L, Szterenberg L, Lis T (2006) Angew Chem Int Ed 45:3670
Carré FH, Corriu RJP, Bolin G, Moreau JJE, Vernhet C (1993) Organometallics 12:2478
Corriu RJP, Bolin G, Moreau JJE, Vernhet C (1991) J Chem Soc Chem Commun:211
Abebayehu A, Dutta R, Lee CH (2016) Chem A Eur J 22:13850
Jeong SD, Sessler JL, Lynch V, Lee CH (2008) J Am Chem Soc 130:390
Sengupta R, Thorat KG, Ravikanth M (2018) J Org Chem 83:11794
Brewster JT, He Q, Anguera G, Moore MD, Ke XS, Lynch VM, Sessler JL (2017) Chem Commun 53:4981
Brewster JT, Mangel DN, Gaunt AJ, Saunders DP, Zafar H, Lynch VM, Boreen MA, Garner ME, Goodwin CAP, Settineri NS, Arnold J, Sessler JL (2019) J Am Chem Soc 141:17867
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2020 Springer Nature Switzerland AG
About this chapter
Cite this chapter
Hurej, K., Latos-Grażyński, L. (2020). A Pincer Motif Etched into a meta-Benziporphyrin Frame. In: van Koten, G., Kirchner, K., Moret, ME. (eds) Metal-Ligand Co-operativity. Topics in Organometallic Chemistry, vol 68. Springer, Cham. https://doi.org/10.1007/3418_2020_61
Download citation
DOI: https://doi.org/10.1007/3418_2020_61
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-68915-5
Online ISBN: 978-3-030-68916-2
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)