Charge transfer in mixed and segregated stacks of tetrathiafulvalene, tetrathianaphthalene and naphthalene diimide: a structural, spectroscopic and computational study

Leong, Chanel F.; Chan, Bun; Liu, Tianfu; Moore, Harrison S.; Hod, Idan; Solomon, Marcello B.; Usov, Pavel M.; Hupp, Joseph T.; Farha, Omar; D’Alessandro, Deanna M.

doi:10.1039/d2nj00643j

Title: Charge transfer in mixed and segregated stacks of tetrathiafulvalene, tetrathianaphthalene and naphthalene diimide: a structural, spectroscopic and computational study

Journal Article · Mon Apr 25 00:00:00 EDT 2022 · New Journal of Chemistry

DOI:https://doi.org/10.1039/d2nj00643j· OSTI ID:1978899

Leong, Chanel F. ^[1];

^[2];

^[3]; Moore, Harrison S. ^[1];

^[4];

^[1]; Usov, Pavel M. ^[1];

^[3];

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Univ. of Sydney, NSW (Australia)
Nagasaki University (Japan)
Northwestern Univ., Evanston, IL (United States)
Ben Gurion Univ. of the Negev, Beer Sheva (Israel)

Tetrathiafulvalene (TTF) is a highly tunable electron donor that has been widely studied in charge transfer (CT) complexes, including Bechgaard salts which are superconductors at low temperatures. Its close relative, tetrathianaphthalene (TTN) has received considerably less attention than its TTF counterpart but is potentially a versatile electron donor. Three novel CT complexes containing mixed and segregated stack donor-acceptor (D–A) complexes of tetrathiafulvalene (TTF), tetrathianaphthalene (TTN) and naphthalene diimide (NDI) are reported. We demonstrate a facile mechanochemical synthesis of two salts, TTF–DPNI and TTN–DPNI (DPNI = N,N'-di-(4-pyridyl)-1,4,5,8-naphthalenetetracarboxydiimide), which is uncommon for these materials. Despite the detection of a very low partial charge transfer in the three salts using UV-Vis-NIR, Raman and EPR spectroscopies, we elucidated the properties of the TTN core with support from DFT calculations for the first time. Finally, we highlight the performance of TTN in a CT complex and demonstrate the importance of a combined approach to the characterisation of CT in organic D–A complexes.

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Research Organization:: Northwestern Univ., Evanston, IL (United States); Univ. of Minnesota, Minneapolis, MN (United States)

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

Grant/Contract Number:: FG02-87ER13808; SC0008688; FG02-17ER16362

OSTI ID:: 1978899

Alternate ID(s):: OSTI ID: 1866873

Journal Information:: New Journal of Chemistry, Vol. 46, Issue 21; ISSN 1144-0546

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Title: Charge transfer in mixed and segregated stacks of tetrathiafulvalene, tetrathianaphthalene and naphthalene diimide: a structural, spectroscopic and computational study

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