The Effects of Ring Strain on Cyclic Tetraaryl[5]cumulenes.
Raman spectroscopy
X-ray crystallography
cumulenes
macrocycles
ring strain
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
06 Jul 2022
06 Jul 2022
Historique:
received:
24
02
2022
pubmed:
28
4
2022
medline:
9
7
2022
entrez:
27
4
2022
Statut:
ppublish
Résumé
Cyclic tetraaryl[5]cumulenes (1 a-f) have been synthesized and studied as a function of increasing ring strain. The magnitude of ring strain is approximated by the extent of bending of the cumulenic core as assessed by a combination of X-ray crystallographic analysis and DFT calculations. Trends are observed in
Identifiants
pubmed: 35476301
doi: 10.1002/chem.202200616
doi:
Substances chimiques
Polyenes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200616Subventions
Organisme : Natural Sciences and Engineering Research Council of Canada
ID : RGPIN-2017-05052
Organisme : Compute Canada
Organisme : Canada Foundation for Innovation
ID : 37268
Organisme : Deutsche Forschungsgemeinschaft
ID : SFB 953
Organisme : Horizon 2020
ID : 724610
Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
A. L. Sadowy, R. R. Tykwinski, in Modern Supramolecular Chemistry: Strategies for Macrocycle Synthesis (Eds.: F. Diederich, P. J. Stang, R. R. Tykwinski), Wiley-VCH, 2008, pp. 185-231.
C. E. Colwell, T. W. Price, T. Stauch, R. Jasti, Chem. Sci. 2020, 11, 3923-3930.
F. Sondheimer, Acc. Chem. Res. 1972, 5, 81-91.
E. L. Spitler, C. A. Johnson II, M. M. Haley, Chem. Rev. 2006, 106, 5344-5386.
K. Cocq, C. Lepetit, V. Maraval, R. Chauvin, Chem. Soc. Rev. 2015, 44, 6535-6559.
T. Kawase, H. Kurata, Chem. Rev. 2006, 106, 5250-5273.
M. K. Smith, O. Š. Miljanić, Org. Biomol. Chem. 2015, 13, 7841-7845.
M. Hermann, D. Wassy, B. Esser, Angew. Chem. Int. Ed. 2021, 60, 15743-15766.
K. Tahara, Y. Tobe, Chem. Rev. 2006, 106, 5274-5290.
M. Iyoda, J. Yamakawa, M. J. Rahman, Angew. Chem. Int. Ed. 2011, 50, 10522-10553;
Angew. Chem. 2011, 123, 10708-10740.
Y. Liang, M. Tang, Z. Liu, Chem. Lett. 2020, 49, 1329-1336.
M. A. Majewski, M. Stępień, Angew. Chem. Int. Ed. 2019, 58, 86-116;
Angew. Chem. 2019, 131, 90-122.
S. Liu, Y. Lei, X. Qi, Y. Lan, J. Phys. Chem. A 2014, 118, 2638-2645.
Y. Xu, M. von Delius, Angew. Chem. Int. Ed. 2020, 59, 559-573;
Angew. Chem. 2020, 132, 567-582.
K. Miki, K. Ohe, Chem. Eur. J. 2020, 26, 2529-2575.
E. J. Leonhardt, R. Jasti, Nat. Chem. Rev. 2019, 3, 672-686.
F. Liebman, A. Greenberg, Chem. Rev. 1976, 76, 311-365.
H. L. Anderson, C. W. Patrick, L. M. Scriven, S. L. Woltering, Bull. Chem. Soc. Jpn. 2021, 94, 798-811.
Y. Tobe, T. Wakabayashi, in Polyynes: Synthesis, Properties, and Applications; F. Cataldo, Ed.; CRC Press/Taylor & Francis Boca Raton, 2006, 99-125.
C. S. Casari, M. Tommasini, R. R. Tykwinski, A. Milani, Nanoscale 2016, 8, 4414-4435.
Y. Gao, Y. Hou, F. Gordillo Gámez, M. J. Ferguson, J. Casado, R. R. Tykwinski, Nat. Chem. 2020, 12, 1143-1149.
A. E. Boguslavskiy, H. Ding, J. P. Maier, J. Chem. Phys. 2005, 123, 034305.
F. Diederich, Y. Rubin, O. L. Chapman, N. S. Goroff, Helv. Chim. Acta 1994, 77, 1441-1457.
K. Kaiser, L. M. Scriven, F. Schulz, P. Gawel, L. Gross, H. L. Anderson, Science 2019, 365, 1299-1301.
L. M. Scriven, K. Kaiser, F. Schulz, A. J. Sterling, S. L. Woltering, P. Gawel, K. E. Christensen, H. L. Anderson, L. Gross, J. Am. Chem. Soc. 2020, 142, 12921-12924.
A. La Torre, A. Botello-Mendez, W. Baaziz, J. C. Charlier, F. Banhart, Nat. Commun. 2015, 6, 6636-6642.
A. Spantulescu, T. Luu, Y. Zhao, R. McDonald, R. R. Tykwinski, Org. Lett. 2008, 10, 609-612.
R. P. Johnson, Chem. Rev. 1989, 89, 1111-1124.
S. Hernandez, M. M. Kirchhoff, S. G. Swartz, R. P. Johnson, Tetrahedron Lett. 1996, 37, 4907-4910.
R. O. Angus, R. P. Johnson, J. Org. Chem. 1984, 49, 2880-2883.
For prior examples of unstrained, cyclic tetraalkyl[5]cumulenes, see T. Negi, T. Kaneda, H. Mizuno, T. Toyoda, Y. Sakata, S. Misumi, Bull. Chem. Soc. Jpn. 1974, 47, 2398-2405.
J. A. Januszewski, R. R. Tykwinski, Chem. Soc. Rev. 2014, 43, 3184-3203.
D. Wendinger, R. R. Tykwinski, Acc. Chem. Res. 2017, 50, 1468-1479.
L. Balas, T. Durand, S. Saha, I. Johnson, S. Mukhopadhyay, J. Med. Chem. 2009, 52, 1005-1017.
J. L. Marshall, D. Lehnherr, B. D. Lindner, R. R. Tykwinski, ChemPlusChem 2017, 82, 967-1001.
M. Gholami, R. R. Tykwinski, Chem. Rev. 2006, 106, 4997-5027.
H. D. Hartzler, J. Am. Chem. Soc. 1971, 93, 4527-4531.
N. Islam, T. Ooi, T. Iwasawa, M. Nishiuchi, Y. Kawamura, Chem. Commun. 2009, 574-576.
D. Wendinger, J. A. Januszewski, F. Hampel, R. R. Tykwinski, Chem. Commun. 2015, 51, 14877-14880.
Y. Kuwatani, G. Yamamoto, M. Oda, M. Iyoda, Bull. Chem. Soc. Jpn. 2005, 78, 2188-2208.
K. J. Daoust, S. M. Hernandez, K. M. Konrad, I. D. Mackie, J. Winstanley Jr., R. P. Johnson, J. Org. Chem. 2006, 71, 5708-5714.
Deposition Numbers 2089313 (for 1 a), 2089314 (for 1 b), 2089315 (for 1 c), 2089892 (for 1 d), 2089893 (for 1 e) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
J. A. Januszewski, D. Wendinger, C. D. Methfessel, F. Hampel, R. R. Tykwinski, Angew. Chem. Int. Ed. 2013, 52, 1817-1821;
Angew. Chem. 2013, 125, 1862-1867.
C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158-6169.
T. H. Dunning Jr., J. Chem. Phys. 1989, 90, 1007-1023.
S. E. Wheeler, WIREs Comput. Mol. Sci. 2012, 2, 204-220.
For theoretical predictions, see: K. B. Wiberg, J. D. Hammer, K. W. Zilm, J. R. Cheeseman, J. Org. Chem. 1999, 64, 6394-6400.
R. R. Tykwinski, T. Luu, Synthesis 2012, 44, 1915-1922.
A. Ehnbom, M. B. Hall, J. A. Gladysz, Org. Lett. 2019, 21, 753-757.
S. Eisler, R. McDonald, G. R. Loppnow, R. R. Tykwinski, J. Am. Chem. Soc. 2000, 122, 6917-6928.
This analysis is adapted from linear [n]cumulenes (see Ref. [52]) and is, of course, an over simplification, but it allows the formal designation of the two π-systems that dominate the electronic characteristics of these molecules.
M. Franz, J. A. Januszewski, D. Wendinger, C. Neiss, L. D. Movsisyan, F. Hampel, H. L. Anderson, A. Görling, R. R. Tykwinski, Angew. Chem. Int. Ed. 2015, 54, 6645-6649;
Angew. Chem. 2015, 127, 6746-6750.
The electronic absorption spectra of unstrained, cyclic tetraalkyl[5]cumulenes has been described, see Ref. [31].
Y. H. Hu, J. Phys. Chem. C 2011, 115, 1843-1850.
A. Lucotti, M. Tommasini, W. A. Chalifoux, D. Fazzi, G. Zerbi, R. R. Tykwinski, J. Raman Spectrosc. 2012, 43, 95-101.
C. Castiglioni, M. Tommasini, G. Zerbi, Philos. Trans. R. Soc. A 2004, 362, 2425-2459.
M. Tommasini, A. Milani, D. Fazzi, A. Lucotti, C. Castiglioni, J. A. Januszewski, D. Wendinger, R. R. Tykwinski, J. Phys. Chem. C 2014, 118, 26415-26425.
A. Troisi, A. Shaw, J. Phys. Chem. Lett. 2016, 7, 4689-4694.
See Supporting Information for synthetic details.
M. U. Bühringer, K. Padberg, M. D. Phleps, H. Maid, C. Placht, C. Neiss, M. J. Ferguson, A. Görling, R. R. Tykwinski, Angew. Chem. Int. Ed. 2018, 57, 8321-8325;
Angew. Chem. 2018, 130, 8454-8458.