Article Planar versus Twist: Two Conformers of a 5,7,12,14-Tetrakis(triisopropylsilylethynyl)pentacene in the Solid State

Satoshi Tanaka ; Ryoko Oyama ; Mitsuharu Suzuki ORCID ; Hironobu Hayashi SAMURAI ORCID ; Hiroko Yamada ORCID ; Naoki Aratani ORCID

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Satoshi Tanaka, Ryoko Oyama, Mitsuharu Suzuki, Hironobu Hayashi, Hiroko Yamada, Naoki Aratani. Planar versus Twist: Two Conformers of a 5,7,12,14-Tetrakis(triisopropylsilylethynyl)pentacene in the Solid State. Organic Letters. 2025, 27 (44), 12255-12258. https://doi.org/10.1021/acs.orglett.5c03674

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(abstract)

We synthesized 4TIPS-pen, a pentacene derivative bearing TIPS-ethynyl groups at the 5,7,12,14-positions via a modified route. The compound showed polymorphism, forming green crystals with a twisted backbone and blue crystals with a planar backbone. UV–vis spectra and theoretical calculations revealed distinct optical behaviors linked to structural differences. 4TIPS-pen is photounstable, and we confirmed the product structure using X-ray analysis. These results highlight structure–property relationships and offer design guidelines for extended π-conjugated pentacenes.

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Keyword: aromatic compounds, crystal structure, crystals, hydrocarbon, reaction product

Date published: 2025-11-07

Publisher: American Chemical Society (ACS)

Journal:

  • Organic Letters (ISSN: 15237060) vol. 27 issue. 44 p. 12255-12258

Funding:

  • Nara Institute of Science and Technology
  • Ministry of Education, Culture, Sports, Science and Technology JPMXP1225NR5003
  • Casio Science Promotion Foundation J41-23
  • Ministry of Education, Culture, Sports, Science and Technology JP20H05833
  • Ministry of Education, Culture, Sports, Science and Technology JP23K26480
  • Ministry of Education, Culture, Sports, Science and Technology JP24K01553
  • Ministry of Education, Culture, Sports, Science and Technology JP24K01576
  • Ministry of Education, Culture, Sports, Science and Technology JP24K23087
  • Ministry of Education, Culture, Sports, Science and Technology JP25K01751
  • Masuyakinen basic research foundation

Manuscript type: Publisher's version (Version of record)

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First published URL: https://doi.org/10.1021/acs.orglett.5c03674

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Updated at: 2025-12-10 12:30:06 +0900

Published on MDR: 2025-12-10 12:23:55 +0900

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