Abstract
The four pyrrole rings and four meso carbons of tetrapyrrolic porphyrins can be arranged in different ways and the resulting porphyrin isomers exhibit very distinct electronic properties. The extensive research carried out on the porphyrins over the years has revealed that porphyrin can have several possible isomers and some of these have been identified and synthesized. Among the porphyrin isomers synthesized so far, porphycene and N-confused porphyrins have been investigated extensively whereas the other porphyrin isomers such as hemiporphycene, corrphycene and isoporphycene remain underdeveloped because of synthetic difficulties and their inherently unstable nature. Neoporphyrinoids are new members of the porphyrinoid family that were discovered serendipitously in 2011. Neoporphyrinoids are structural analogues of porphyrinoids with a confused pyrrole nitrogen linked to a meso carbon or the adjacent pyrrole carbon. Thus, neoporphyrinoids have an unusual structure in which pyrrole N is a part of a porphyrinoid framework and the lone pair of electrons on nitrogen participate in macrocyclic conjugation. It's been a decade since the discovery and different types of neoporphyrinoids, including regular, contracted and expanded neoporphyrinoids, have been synthesized by rational synthetic methodologies and their spectral, structural, aromatic and coordination properties have been studied. There is huge scope to develop different synthetic routes to produce new types of stable neoporphyrinoids to study their properties and potential applications. This article presents a brief overview of the synthesis, structure and properties of the neoporphyrinoids reported in this decade.
Similar content being viewed by others
References
Drain CM, Varotto A, Radivojevic I (2009) Chem Rev 109:1630
Shubina TE, Marbach H, Flechtner K, Kretschmann A, Jux N, Buchner F, Steinrück H-P, Clark T, Gottfried JM (2007) J Am Chem Soc 129:9476
Barbieri A, Bandini E, Monti F, Praveen VK, Armaroli N (2016) Top Curr Chem 374:47
Chatterjee T, Ravikanth M (2020) Coord Chem Rev 422:213480
Wong W-K, Zhu X, Wong W-Y (2007) Coord Chem Rev 251:2386
Meunier B (1992) Chem Rev 92:1411
Yao Y, Hou C-L, Yang Z-S, Ran G, Kang L, Li C, Zhang W, Zhang J, Zhang J-L (2019) Chem Sci 10:10170
Ning Y, Jin G-Q, Zhang J-L (2019) Acc Chem Res 52:2620
Ethirajan M, Chen Y, Joshi P, Pandey RK (2011) Chem Soc Rev 40:340
Li L-L, Diau EW-G (2013) Chem Soc Rev 42:291
Jin G-Q, Xue H-Z, Zhang J-L (2021) Chem Plus Chem 86:71
Bodedla GB, Tang G, Zhao J, Zhu X (2020) Sustain Energy Fuels 4:2675
Tritton DN, Bodedla GB, Tang G, Zhao J, Kwan C-S, Leung KC-F, Wong W-Y, Zhu X (2020) J Mater Chem A 8:3005
Punnagai M, Joseph S, Sastry GN (2004) J Chem Sci 116:271
Wu Y-D, Chan KWK, Yip C-P, Vogel E, Plattner DA, Houk KN (1997) J Org Chem 62:9240
Ghosh A, Jynge K (1997) J Phys Chem B 101:5459
Vogel E, Köcher M, Schmickler H, Lex J (1986) Angew Chem Int Ed 25:257
Waluk J (2017) Chem Rev 117:2447
Sánchez-García D, Sessler JL (2008) Chem Soc Rev 37:215
Sessler JL, Brucker EA, Weghorn SJ, Kisters M, Schäfer M, Lex J, Vogel E (1994) Angew Chem Int Ed 33:2308
Neya S, Nishinaga K, Ohyama K, Funasaki N (1998) Tetrahedron Lett 39:5217
Vogel E, Bröring M, Weghorn SJ, Scholz P, Deponte R, Lex J, Schmickler H, Schaffner K, Braslavsky SE, Müller M, Pörting S, Sessler JL, Fowler CJ (1997) Angew Chem Int Ed 36:1651
Vogel E, Scholz P, Demuth R, Erben C, Bröring M, Schmickler H, Lex J, Hohlneicher G, Bremm D, Wu Y-D (1999) Angew Chem Int Ed 38:2919
Toganoh M, Furuta H (2012) Chem Comm 48:937
Chmielewski PJ, Latos-Grażyński L, Rachlewicz K, Glowiak T (1994) Angew Chem Int Ed 33:779
Furuta H, Asano T, Ogawa T (1994) J Am Chem Soc 116:767
Lash TD (2017) Chem Rev 117:2313
Srinivasan A, Furuta H (2005) Acc Chem Res 38:10
Furuta H, Ishizuka T, Osuka A, Ogawa T (1999) J Am Chem Soc 121:2945
Lash TD, Lammer AD, Ferrence GM (2011) Angew Chem Int Ed 50:9718
Fujino K, Hirata Y, Kawabe Y, Morimoto T, Srinivasan A, Toganoh M, Miseki Y, Kudo A, Furuta H (2011) Angew Chem Int Ed 50:6855
Li R, Lammer AD, Ferrence GM, Lash TD (2014) J Org Chem 79:4078
Li R, Ferrence GM, Lash TD (2013) Chem Comm 49:7537
AbuSalim DI, Lash TD (2015) J Phys Chem A 119:11440
Cao H-Y, Si D-H, Tang Q, Zheng X-F, Hao C (2016) Comput Theor Chem 1081:18
AbuSalim DI, Lash TD (2013) Org Biomol Chem 11:8306
Orłowski R, Gryko D, Gryko DT (2017) Chem Rev 117:3102
Aviv-Harel I, Gross Z (2009) Chem Euro J 15:8382
Barata JFB, Neves MGPMS, Faustino MAF, Tomé AC, Cavaleiro JAS (2017) Chem Rev 117:3192
Umasekhar B, Shetti VS, Ravikanth M (2018) RSC Adv 8:21100
Maurya YK, Noda K, Yamasumi K, Mori S, Uchiyama T, Kamitani K, Hirai T, Ninomiya K, Nishibori M, Hori Y, Shiota Y, Yoshizawa K, Ishida M, Furuta H (2018) J Am Chem Soc 140:6883
Toganoh M, Kawabe Y, Uno H, Furuta H (2012) Angew Chem Int Ed 51:8753
Saltsman I, Mahammed A, Goldberg I, Tkachenko E, Botoshansky M, Gross Z (2002) J Am Chem Soc 124:7411
Gross Z, Galili N, Saltsman I (1999) Angew Chem Int Ed 38:1427
Ryan A, Gehrold A, Perusitti R, Pintea M, Fazekas M, Locos OB, Blaikie F, Senge MO (2011) Eur J Org Chem 2011:5817
Osuka A, Shimidzu H (1997) Angew Chem Int Ed 36:135
Ishizuka T, Osuka A, Furuta H (2004) Angew Chem Int Ed 43:5077
Toganoh M, Kawabe Y, Furuta H (2011) J Org Chem 76:7618
Setsune J-I, Tsukajima A, Okazaki N (2009) J Por Phthal 13:256
Tortora L, Nardis S, Fronczek FR, Smith KM, Paolesse R (2011) Chem Commun 47:4243
Pushpanandan P, Maurya YK, Omagari T, Hirosawa R, Ishida M, Mori S, Yasutake Y, Fukatsu S, Mack J, Nyokong T, Furuta H (2017) Inorg Chem 56:12572
Luobeznova I, Simkhovich L, Goldberg I, Gross Z (2004) Eur J Inorg Chem 2004:1724
Basumatary B, Hashiguchi I, Mori S, Shimizu S, Ishida M, Furuta H (2020) Angew Chem Int Ed Ed 59:15897
Adinarayana B, Thomas AP, Suresh CH, Srinivasan A (2015) Angew Chem Int Ed 54:10478
Furuta H, Maeda H, Osuka A (2000) J Am Chem Soc 122:803
Xie Y, Wei P, Li X, Hong T, Zhang K, Furuta H (2013) J Am Chem Soc 135:19119
Maurya YK, Ishikawa T, Kawabe Y, Ishida M, Toganoh M, Mori S, Yasutake Y, Fukatsu S, Furuta H (2016) Inorg Chem 55:6223
Saito S, Osuka A (2011) Angew Chem Int Ed 50:4342
Stępień M, Sprutta N, Latos-Grażyński L (2011) Angew Chem Int Ed 50:4288
Roznyatovskiy VV, Lee C-H, Sessler JL (2013) Chem Soc Rev 42:1921
Chatterjee T, Shetti VS, Sharma R, Ravikanth M (2017) Chem Rev 117:3254
Szyszko B, Białek MJ, Pacholska-Dudziak E, Latos-Grażyński L (2017) Chem Rev 117:2839
Tanaka T, Osuka A (2017) Chem Rev 117:2584
Gadekar SC, Reddy BK, Anand VG (2013) Angew Chem Int Ed 52:7164
Chatterjee T, Srinivasan A, Ravikanth M, Chandrashekar TK (2017) Chem Rev 117:3329
Malakalapalli RR, Mangalampalli R (2012) Tetrahedron 68:1306
Bauer VJ, Clive DLJ, Dolphin D, Paine JB, Harris FL, King MM, Loder J, Wang SWC, Woodward RB (1983) J Am Chem Soc 105:6429
Mori D, Yoneda T, Hoshino T, Neya S (2018) Chem Asian J 13:934
Pareek Y, Ravikanth M, Chandrashekar TK (2012) Acc Chem Res 45:1801
Sessler JL, Davis JM, Lynch V (1998) J Org Chem 63:7062
Li Q, Li C, Kim J, Ishida M, Li X, Gu T, Liang X, Zhu W, Ågren H, Kim D, Furuta H, Xie Y (2019) J Am Chem Soc 141:5294
Xie D, Liu Y, Rao Y, Kim G, Zhou M, Yu D, Xu L, Yin B, Liu S, Tanaka T, Aratani N, Osuka A, Liu Q, Kim D, Song J (2018) J Am Chem Soc 140:16553
Kalita H, Lee W-Z, Ravikanth M (2013) J Org Chem 78:6285
Kalita H, Lee W-Z, Ravikanth M (2013) Dalton Trans 42:14537
Wei P, Zhang K, Li X, Meng D, Ågren H, Ou Z, Ng S, Furuta H, Xie Y (2014) Angew Chem Int Ed 53:14069
Zhang K, Zhang J, Li X, Guo R, Ågren H, Ou Z, Ishida M, Furuta H, Xie Y (2015) Org Lett 17:4806
Acknowledgments
M.R. thanks Wadhwani Research Center for Bioengineering (WRCB), IIT Bombay for financial support. P.P. thanks IIT Bombay for granting an institute post-doctoral fellowship.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Pushpanandan, P., Ravikanth, M. Neo-Porphyrinoids: New Members of the Porphyrinoid Family. Top Curr Chem (Z) 379, 26 (2021). https://doi.org/10.1007/s41061-021-00338-6
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s41061-021-00338-6