Editorial pubs.acs.org/CR
Introduction: Expanded, Contracted, and Isomeric Porphyrins
I
This is a very deep, and rather dense thematic issue. A summary of each contribution in a preface such as this would necessarily be so terse as to be worthless. So, rather than devalue the rich intellectual contributions of the authors, we as Editors would like you to cozy up in your favorite chair with a beverage of choice in hand and peruse the list of articles. Then, as your interest is tickled, dig in. By reading deeply, acquaint yourself further or for the first time with the fascinating world of nonporphyrin macrocycles. If you are new to the field, we hope you will soon be hooked. In fact, in short order we expect you will be contributing to the accelerating growth of this highly addictive area. There is already something for everyone, but it is a field that is far from being fully explored. The best is yet to come. Happy reading!
n 1997 one of the Guest Editors of this thematic issue (Sessler) had the distinct pleasure of writing a monograph with Steve Weghorn on “Expanded, Contracted, and Isomeric Porphyrins.” This was roughly a decade after the late, great Emanuel Vogel’s seminal report of porphycene, the first characterized porphyrin isomer, and not even 10 years subsequent to the Sessler group coining the term “expanded porphyrin” in the context of reporting the first texaphyrin. While others will have to judge, it is possible that this monograph played a key role in defining the field of nonporphyrin analogues as being worthy of study. Independent of the triggers, the field has blossomed. In 1997 it was still possible to summarize just about everything published in the area. However, that was only true because many of the seminal discoveries that have animated the field had not yet been made. Synthetic methodologies were still limited. Corroles could only be obtained through laborious synthesis; with the exception of nonaromatic rosarins, mesosubstituted expanded porphyrins were beyond anyone’s imagination, as were direct coupling strategies to produce meso-free systems, such as the cyclo[n]pyrroles. Anion recognition was limited to protonated expanded porphyrins, and N-confusion as a way of creating isomers of porphyrins and higher order species was not on anyone’s radar. Advances in aromaticity, including Möbius (anti)aromaticity, heteroatom substitution, and most of the known coordination chemistry, had yet to be conceived. Apart from singlet oxygen generation in a few instances, the excited state features of porphyrin analogues had yet to be explored. Much more was unknown in 1997 than was known! Twenty years after the original Sessler−Weghorn monograph, it would be impossible to summarize the field of nonporphyrin analogues in a single volume. With consistent encouragement (even to the point of gentle prodding) from Guy Bertrand (a Chemical Reviews Associate Editor), the three of us (Sessler, Gross, and Furuta) conceived the idea of the present thematic issue. The idea was that the three of us would help solicit contributions in the areas of expanded, contracted, and isomeric porphyrins, respectively. While acting as Chemical Reviews Guest Editors is not on the level of writing a comprehensive monograph, putting together an issue of this depth and breadth actually turned out to be a herculean task. Fortunately, our wonderful contributors did most of the heavy lifting. We the Editors, for the most part, could sit back and watch amazing contributions come flowing in. Needless to say, we are grateful for all the authors. This success is theirs and reflects the fact that they not only responded enthusiastically to the initial queries, but also voted with their time, as it were, by submitting wonderful reviews. The net result is something in which the authors should take justifiable pride. It is a colorful collage of modern “Expanded, Contracted, and Isomeric Porphyrins”. However, this thematic issue also contains reviews summarizing a variety of other fascinating porphyrin analogues, including those related to phthalocyanines and calixpyrroles. The world of chemistry is richer for the authors’ contributions. We as Guest Editors are in their debt. © 2017 American Chemical Society
Jonathan L. Sessler*
University of Texas at Austin
Zeev Gross* Technion
Hiroyuki Furuta* Kyushu University
AUTHOR INFORMATION Corresponding Authors
Email:
[email protected]. Email:
[email protected]. Email:
[email protected]. ORCID
Jonathan L. Sessler: 0000-0002-9576-1325 Zeev Gross: 0000-0003-1170-2115 Hiroyuki Furuta: 0000-0002-3881-8807 Notes
Views expressed in this editorial are those of the authors and not necessarily the views of the ACS. Biographies
Special Issue: Expanded, Contracted, and Isomeric Porphyrins Published: February 22, 2017 2201
DOI: 10.1021/acs.chemrev.7b00036 Chem. Rev. 2017, 117, 2201−2202
Chemical Reviews
Editorial
Jonathan L. Sessler received a B.S. degree (with Highest Honors) in chemistry in 1977 from the University of California, Berkeley and a Ph.D. in organic chemistry from Stanford University in 1982 (supervisor: Prof. James P. Collman). After completing NSF-CNRS and NSF-NATO Postdoctoral Fellowships with Jean-Marie Lehn at L’Université Louis Pasteur de Strasbourg, France, he was a JSPS Visiting Scientist in Tabushi’s group in Kyoto, Japan. In September 1984, he accepted a position as an Assistant Professor of Chemistry at the University of Texas at Austin, where he currently holds the DohertyWelch Chair. To date, Dr. Sessler has authored over 650 research publications, written two books, and has been an inventor of record on over 75 issued US Patents. Dr. Sessler was a cofounder of Pharmacyclics, Inc., which was acquired by AbbVie in 2015 for $21B, and more recently Cible, Inc. Both companies are dedicated to developing new cancer therapies.
Hiroyuki Furuta received his Ph.D. degree from Kyoto University in 1986 for work on photoinduced electron transfer reaction of porphyrins under the direction of Kazuhiro Maruyama. He then joined the group of Hiroshi Yanagawa at the Mitsubishi-Kasei Institute of Life Sciences, Tokyo, as a Postdoctoral Fellow, where he worked for the prebiotic RNA synthesis. In 1989, he moved to Jonathan L. Sessler’s lab at the University of Texas, Austin as a Postdoctoral Fellow, during which time he explored supramolecular chemistry based on nucleobases and expanded porphyrins. In 1992, he started his independent academic carrier at Oita University as an Associate Professor. While at Oito, Prof. Furuta found a new porphyrin isomer, which he termed “N-confused porphyrin”. In 1997, he moved to Kyoto University as an Associate Professor and worked with Atsuhiro Osuka. In 2002, he was named a Full Professor in Chemistry at Kyushu University. His current research focuses on the synthesis of porphyrin analogues, so-called N-confused porphyrinoids, their multimetal complexes, and their use in the development of novel functional NIR dyes.
Zeev Gross received his Ph.D. in Chemistry from Bar-Ilan University in 1988, for work performed under the guidance of Professor S. Hoz in the field of Physical Organic Chemistry. He then moved to Princeton University for two years as a Fulbright postdoctoral fellow, during which time he explored several aspects of metalloporphyrin chemistry under the guidance of Professor J. T. Groves. In 1990 he accepted a position at the Technion, where he is currently Professor of Chemistry and the incumbent of the Blum Academic Chair. In addition to his primary academic appointment, Prof. Gross is spearheading multiple outreach activities with the goal of encouraging high school students to enroll in chemistry studies. He also serves as the dean of the Division of Continuing and External Studies at the Technion. Since 1999, when his group discovered the first facile synthesis of corroles from pyrrole and aldehydes, the focus of Prof. Gross’ research has centered on uncovering unique features of metallocorroles and their utility in applications of prime importance for modern society, namely discovering new drugs and designing better catalysts for energy-relevant processes.
2202
DOI: 10.1021/acs.chemrev.7b00036 Chem. Rev. 2017, 117, 2201−2202
