Pyrene-Fused Pyrazaacenes with Eight Rectilinearly Arranged Aromatic Rings

Wang, Chuan-Zeng; Feng, Xing; Elsegood, Mark R.  J.; Warwick, Thomas G.; Teat, Simon J.; Redshaw, Carl; Bi, Yu-Sui; Yamato, Takehiko

doi:10.1002/ajoc.201800608

Title: Pyrene-Fused Pyrazaacenes with Eight Rectilinearly Arranged Aromatic Rings

Journal Article · 14 November 2018 · Asian Journal of Organic Chemistry

DOI: https://doi.org/10.1002/ajoc.201800608 · OSTI ID:1579332

Wang, Chuan-Zeng ^[1]; Feng, Xing ^[2];

^[3]; Warwick, Thomas G. ^[3]; Teat, Simon J. ^[4];

^[5]; Bi, Yu-Sui ^[6];

^[7]

Shandong Univ. of Technology, Zibo (China); Saga Univ. (Japan)
Guangdong Univ. of Technology (China)
Loughborough Univ., Loughborough (United Kingdom)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Univ. of Hull, Yorkshire (United Kingdom)
Shandong Univ. of Technology, Zibo (China)
Saga Univ. (Japan)

A series of pyrene-fused azaacene-type conjugated molecules containing two pyrazine units and up to eight rectilinearly arranged aromatic rings were prepared by condensation coupling reactions in moderate yields. The geometries and electronic structures associated with 2 and 5 were evaluated by DFT calculations. Photophysical properties indicated that these systems possess delocalized structures, and their optoelectronic properties can be tuned by extending the π-conjugated length and introducing electronic-withdrawing groups. The compounds were thoroughly investigated by XRD studies, electrochemistry and DFT calculations. High thermal stability and tunable energy levels make them excellent candidates as a class of organic molecular materials.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1579332

Journal Information:: Asian Journal of Organic Chemistry, Journal Name: Asian Journal of Organic Chemistry Journal Issue: 1 Vol. 8; ISSN 2193-5807

Publisher:: Wiley, Asian Chemical Editorial SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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