Twisting the Propotypic Molecules of Ph-C≡C-Ph, Ph-CH═CH-Ph, and Ph-N═N-Ph through Cocrystallization

Yury V. Torubaev; Ivan V. Skabitskiy; Mariela J. Pavan; Doron Pappo

doi:10.1021/acs.cgd.5c00106

Twisting the Propotypic Molecules of Ph-C≡C-Ph, Ph-CH═CH-Ph, and Ph-N═N-Ph through Cocrystallization

Yury V. Torubaev, Ivan V. Skabitskiy, Mariela J. Pavan, Doron Pappo

Department of Chemistry

Ben-Gurion University of the Negev

Research output: Contribution to journal › Article › peer-review

Abstract

Trans-stilbene, trans-azobenzene, and diphenylacetylene are the prototypic models for photochemical and photophysical studies. This work focuses on the structural investigation of their twisting behavior, which may significantly impact their electronic and photophysical properties. Here, we demonstrate the use of supramolecular derivatization to induce twists in these molecules without chemical modification using π···π-hole interactions with decafluorobiphenyl (FBPh). Cocrystallization with FBPh resulted in twisted conformations, which are further relaxed to the plane conformation in the melt.

Original language	American English
Journal	Crystal Growth and Design
DOIs	https://doi.org/10.1021/acs.cgd.5c00106
State	Accepted/In press - 1 Jan 2025

All Science Journal Classification (ASJC) codes

General Chemistry
General Materials Science
Condensed Matter Physics

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10.1021/acs.cgd.5c00106

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title = "Twisting the Propotypic Molecules of Ph-C≡C-Ph, Ph-CH═CH-Ph, and Ph-N═N-Ph through Cocrystallization",

abstract = "Trans-stilbene, trans-azobenzene, and diphenylacetylene are the prototypic models for photochemical and photophysical studies. This work focuses on the structural investigation of their twisting behavior, which may significantly impact their electronic and photophysical properties. Here, we demonstrate the use of supramolecular derivatization to induce twists in these molecules without chemical modification using π···π-hole interactions with decafluorobiphenyl (FBPh). Cocrystallization with FBPh resulted in twisted conformations, which are further relaxed to the plane conformation in the melt.",

author = "Torubaev, {Yury V.} and Skabitskiy, {Ivan V.} and Pavan, {Mariela J.} and Doron Pappo",

note = "Publisher Copyright: {\textcopyright} 2025 The Authors. Published by American Chemical Society.",

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doi = "10.1021/acs.cgd.5c00106",

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AU - Torubaev, Yury V.

AU - Skabitskiy, Ivan V.

AU - Pavan, Mariela J.

AU - Pappo, Doron

PY - 2025/1/1

Y1 - 2025/1/1

N2 - Trans-stilbene, trans-azobenzene, and diphenylacetylene are the prototypic models for photochemical and photophysical studies. This work focuses on the structural investigation of their twisting behavior, which may significantly impact their electronic and photophysical properties. Here, we demonstrate the use of supramolecular derivatization to induce twists in these molecules without chemical modification using π···π-hole interactions with decafluorobiphenyl (FBPh). Cocrystallization with FBPh resulted in twisted conformations, which are further relaxed to the plane conformation in the melt.

AB - Trans-stilbene, trans-azobenzene, and diphenylacetylene are the prototypic models for photochemical and photophysical studies. This work focuses on the structural investigation of their twisting behavior, which may significantly impact their electronic and photophysical properties. Here, we demonstrate the use of supramolecular derivatization to induce twists in these molecules without chemical modification using π···π-hole interactions with decafluorobiphenyl (FBPh). Cocrystallization with FBPh resulted in twisted conformations, which are further relaxed to the plane conformation in the melt.

UR - http://www.scopus.com/inward/record.url?scp=105002735278&partnerID=8YFLogxK

U2 - 10.1021/acs.cgd.5c00106

DO - 10.1021/acs.cgd.5c00106

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JF - Crystal Growth and Design

ER -

Twisting the Propotypic Molecules of Ph-C≡C-Ph, Ph-CH═CH-Ph, and Ph-N═N-Ph through Cocrystallization

Abstract

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