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Absorption spectra of calix[3]pyrrole analogs as probes for contracted macrocycles

Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, Japan

These authors contributed equally to this work.

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Ranajit Saha

Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan

These authors contributed equally to this work.

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Yuya Inaba

Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, Japan

SPP full member in good standing.

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Yumehiro Manabe

Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, Japan

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Tomoki Yoneda

Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, Japan

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Yuki Ide

Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan

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Yuh Hijikata

Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan

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, and

Yasuhide Inokuma

Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido 060-8628, Japan

Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan

E-mail Address: inokuma@eng.hokudai.ac.jp

Correspondence to: Yasuhide Inokuma, tel: +81-(0)11-706-6556, fax: +81-(0)11-706-6557.

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https://doi.org/10.1142/S1088424622500754Cited by:4 (Source: Crossref)

Abstract

Calix[3]pyrrole and its furan derivatives exhibited bathochromically shifted lowest-energy electronic transition bands in their absorption spectra compared with their calix[4]- and calix[6]-pyrrole analogues, despite the repeating units being the same. We also observed fluorescence emission for calix[3]-type macrocycles. The Stokes shift of the furan/pyrrole hybrid macrocycles, calix[2]furan[1]-pyrrole, and calix[1]furan[2]pyrrole, substantially varied depending on the solvent polarity. Non-covalent interaction (NCI) analyses indicated enhanced interactions between neighboring aromatic rings in the calix[3]pyrrole macrocycle, whereas such interactions were weak in calix[4]pyrrole, in which the interchromophore distance is remarkably longer than in calix[3]pyrrole. Theoretical analyses indicated that the red-shifted, lowest-energy bands of calix[3]pyrrole correspond to HOMO–LUMO transitions, the energy gap of which was narrow compared with calix[4]pyrroles. The characteristic absorption bands for calix[3]pyrrole and its related macrocycles are useful as probes for distinguishing such macrocycles from higher calix[ $n$ ]pyrrole ( $n \geq$ 4) analogues that exhibit almost identical absorption spectra.

Dedicated to Prof. Tomás Torres on the occasion of his 70^th birthday

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References

1. Meller A and Ossko A. Monatsh. Chem. 1972; 103: 150–155. Crossref, Web of Science, Google Scholar
2. Inokuma Y, Kwon JH, Ahn TK, Yoo M-C, Kim D and Osuka A. Angew. Chem. Int. Ed. 2006; 45: 961–964. Crossref, Web of Science, Google Scholar
3. Shimizu S , Chem. Rev. 2017; 117: 2730–2784. Crossref, Web of Science, Google Scholar
4. Osuka A, Tsurumaki E and Tanaka T. Bull. Chem. Soc. Jpn. 2011; 84: 679–697. Crossref, Web of Science, Google Scholar
5. Claessens GC, González-Rodríguez D and Torres T. Chem. Rev. 2002; 102: 835–853. Crossref, Web of Science, Google Scholar
6. Dowds M and Nielsen MB. Mol. Syst. Des. Eng. 2021, 6, 6–24. Crossref, Web of Science, Google Scholar
7. Claessens GC, Gonzáles-Rodríuez D, Iglesias SR and Torres T. C. R. Chimie. 2006; 9: 1094–1099. Crossref, Web of Science, Google Scholar
8. Rodríguez-Morgade MS, Esperanza S, Torres T and Barberá J . Chem. Eur. J. 2005; 11: 354–360. Crossref, Web of Science, Google Scholar
9. Prasannan D and Ravikanth M . Coord. Chem. Rev. 2020; 407: 213172. Crossref, Web of Science, Google Scholar
10. Remiro-Buenamañana S, Díaz-Moscoso A, Hughes LD, Bochmann M, Tizzard JG, Coles JS and Cammidge NA. Angew. Chem. Int. Ed. 2015; 54: 7510–7514. Crossref, Web of Science, Google Scholar
11. Kuzuhara D, Sakakibara Y, Mori S, Okujima T, Uno H, Yamada H . Angew. Chem. Int. Ed. 2013; 53: 3360–3363. Crossref, Web of Science, Google Scholar
12. Pawlicki M, Garbicz M, Szterenberg L, Latos- Grażyński L . Angew. Chem. Int. Ed. 2015; 54: 1906–1909. Crossref, Web of Science, Google Scholar
13. Myśliborski R, Latos-Grażyński L, Szterenberg L, Lis T . Angew. Chem. Int. Ed. 2006; 45: 3670–3674. Crossref, Web of Science, Google Scholar
14. Inaba Y, Nomata Y, Ide Y, Pirillo J and Hijikata Y, Yoneda T, Osuka AL, Sessler J, Inokuma Y . J. Am Chem. Soc. 2021; 143: 12355–12360. Crossref, Web of Science, Google Scholar
15. Inaba Y, Kakibayashi Y, Ide Y, Pirillo J, Hijikata Y, Yoneda T and Inokuma Y . Chem. Eur. J. 2022; 28: e202200056. Crossref, Web of Science, Google Scholar
16. Tanaka T and Osuka A . Chem. Rev. 2017; 117: 2584–2640. Crossref, Web of Science, Google Scholar
17. Liu K, Guo Y, Xu J, Shao JS and Jiang XS. Chin. Chem. Lett. 2006; 17: 387–390. Web of Science, Google Scholar
18. Corsini A and Panoyan MJ. J. Inorg. Nucl. Chem. 1977; 39: 1449–1450. Crossref, Web of Science, Google Scholar
19. Rothemund P and Gage LC. J. Am. Chem. Soc. 1955; 77: 3340–3342. Crossref, Web of Science, Google Scholar
20. Cafeo G, Kohnke FH, La Torre GL, White AJP and Williams DJ. Angew. Chem. Int. Ed. 2000; 39: 1496–1498. Crossref, Web of Science, Google Scholar
21. Maupilier W, Journot G, Stoekli-Evans H and Neier R . Eur. J. Org. Chem. 2017: 6023–6037. Crossref, Web of Science, Google Scholar
22. Healy SM, Rest AJ. J. Chem. Soc., Perkin Trans, 1. 1985: 973–982. Crossref, Google Scholar
23. Licciulli S, Aldahiky K, Fomitcheva V, Korobkov I and Gambarottam Duchateau R . Angew. Chem. Int. Ed. 2011; 50: 2346–2349. Crossref, Web of Science, Google Scholar
24. Davis GA, Julia L and Yazdi NS. J. Chem. Soc., Perkin Trans. 2 1989: 239–244. Crossref, Google Scholar
25. Gaussian 16, Revision C.01, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA. Jr, Peralta J. E, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB and Fox DJ. Gaussian, Inc., Wallingford CT, 2016. Google Scholar
26. Johnson RE, Keinan S, Mori-Sánchez P, Contreras-García J, Cohen JA and Yang W . J. Am. Chem. Soc. 2010; 132: 6498–6506. Crossref, Web of Science, Google Scholar
27. Contreras-García J, Johnson RE, Keinan S, Chaudret R, Piquemal J-P, Baratan ND and Yang W . J. Chem. Theory Comput. 2011; 7: 625–632. Crossref, Web of Science, Google Scholar
28. Boto AR, Peccati F, Laplaza R, Quan C, Carbone A, Piquemal J-P, Maday Y and Contreras-García J . J. Chem. Theory Comput. 2020; 16: 4150–4158. Crossref, Web of Science, Google Scholar
29. Boto AR, Peccati F, Laplaza R, Quan C, Carbone A, Piquemal J-P, Maday Y and Contreras-Garcia J. NCIPLOT4: A new step towards a fast quantification of noncovalent interactions, https://github.com/juliacontrerasgarcia/nciplot, last accessed: 11th September 2022. Google Scholar
30. Mataga N, Kaifu Y and Koizumi M . Bull. Chem. Soc. 1956; 29: 465–470. Crossref, Web of Science, Google Scholar
31. Tsuji T, Ohkita M, Konno T and Nishida S . J. Am. Chem. Soc. 1997; 119: 8425–8431. Crossref, Web of Science, Google Scholar
32. Hermann M, Wassy D, Kratzert D and Esser B . Chem. Eur. J. 2018; 24: 7374–7387. Crossref, Web of Science, Google Scholar
33. Biswas S, Qiu SC, Dawe NL, Zhao Y and Bodwell JG . Angew. Chem. Int. Ed. 2019; 58: 9166–9170. Crossref, Web of Science, Google Scholar