In:
Bulletin of the Chemical Society of Japan, Oxford University Press (OUP), Vol. 97, No. 1 ( 2024-01-11)
Abstract:
A doubly annulated cycloparaphenylene (CPP), in which two [N]paraphenylenes share one benzene unit by meta (m)-connection, m-,m-phenylene-[2N] CPP with N = 5 (2a), was synthesized by double annulation between a CPP precursor and 1,5-dibromo-2,4-diiodobenzene followed by reductive aromatization. The structure of 2a was confirmed by NMR, mass spectroscopy, and single crystal X-ray diffraction analysis. As 2a has a figure-eight structure, it can have a twisted Möbius topology. However, the X-ray analysis clearly reveals a non-twisted Hückel topology in a solid state. The photophysical and electrochemical properties of 2a were also clarified. The studies proved that, while 2a can also be seen as ortho (o)-,o- or para (p)-,p-connected [10]CPP, 2a has an meta (m)-,m-connected electronic structure. The theoretical calculations also support this conclusion.
Type of Medium:
Online Resource
ISSN:
0009-2673
,
1348-0634
DOI:
10.1093/bulcsj/uoad011
Language:
English
Publisher:
Oxford University Press (OUP)
Publication Date:
2024
detail.hit.zdb_id:
2041163-7
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