Host-guest chemistry aids and abets a stereospecific photodimerization in the solid state

Dafni G. Amirsakis; Miguel A. Garcia-Garibay; Stuart J. Rowan; J. Fraser Stoddart; Andrew J P White; David J. Williams

doi:10.1002/1521-3773(20011119)40:22<4256::AID-ANIE4256>3.0.CO;2-S

Host-guest chemistry aids and abets a stereospecific photodimerization in the solid state

Dafni G. Amirsakis, Miguel A. Garcia-Garibay^*, Stuart J. Rowan, J. Fraser Stoddart, Andrew J P White, David J. Williams

^*Corresponding author for this work

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

96 Citations (Scopus)

Abstract

A bis(dialkylammonium ion)-substituted stilbene derivative cocrystallizes with bisparaphenylene[34]crown-10 to form, in the solid state, a 2:2 host-guest complex wherein the stilbene double bonds are aligned with a relative geometry suitable for a stereospecific photochemical [2+2] cycloaddition. When irradiated with white light, this crystalline complex forms a single diastereoisomer of the corresponding cyclobutane derivative (see schematic presentation), the stereo-chemistry of which has been determined unambiguously in the solid state by X-ray crystallography to be syn-anti-syn.

Original language	English
Pages (from-to)	4256-4261
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	40
Issue number	22
DOIs	https://doi.org/10.1002/1521-3773(20011119)40:22<4256::AID-ANIE4256>3.0.CO;2-S
Publication status	Published - 2001 Nov 19
Externally published	Yes

Keywords

Photochemistry
Pseudorotaxanes
Self-assembly
Solid-state reactions
Template synthesis

ASJC Scopus subject areas

Chemistry(all)

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/1521-3773(20011119)40:22<4256::AID-ANIE4256>3.0.CO;2-S

Cite this

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title = "Host-guest chemistry aids and abets a stereospecific photodimerization in the solid state",

abstract = "A bis(dialkylammonium ion)-substituted stilbene derivative cocrystallizes with bisparaphenylene[34]crown-10 to form, in the solid state, a 2:2 host-guest complex wherein the stilbene double bonds are aligned with a relative geometry suitable for a stereospecific photochemical [2+2] cycloaddition. When irradiated with white light, this crystalline complex forms a single diastereoisomer of the corresponding cyclobutane derivative (see schematic presentation), the stereo-chemistry of which has been determined unambiguously in the solid state by X-ray crystallography to be syn-anti-syn.",

keywords = "Photochemistry, Pseudorotaxanes, Self-assembly, Solid-state reactions, Template synthesis",

author = "Amirsakis, {Dafni G.} and Garcia-Garibay, {Miguel A.} and Rowan, {Stuart J.} and {Fraser Stoddart}, J. and White, {Andrew J P} and Williams, {David J.}",

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T1 - Host-guest chemistry aids and abets a stereospecific photodimerization in the solid state

AU - Amirsakis, Dafni G.

AU - Garcia-Garibay, Miguel A.

AU - Rowan, Stuart J.

AU - Fraser Stoddart, J.

AU - White, Andrew J P

AU - Williams, David J.

PY - 2001/11/19

Y1 - 2001/11/19

N2 - A bis(dialkylammonium ion)-substituted stilbene derivative cocrystallizes with bisparaphenylene[34]crown-10 to form, in the solid state, a 2:2 host-guest complex wherein the stilbene double bonds are aligned with a relative geometry suitable for a stereospecific photochemical [2+2] cycloaddition. When irradiated with white light, this crystalline complex forms a single diastereoisomer of the corresponding cyclobutane derivative (see schematic presentation), the stereo-chemistry of which has been determined unambiguously in the solid state by X-ray crystallography to be syn-anti-syn.

AB - A bis(dialkylammonium ion)-substituted stilbene derivative cocrystallizes with bisparaphenylene[34]crown-10 to form, in the solid state, a 2:2 host-guest complex wherein the stilbene double bonds are aligned with a relative geometry suitable for a stereospecific photochemical [2+2] cycloaddition. When irradiated with white light, this crystalline complex forms a single diastereoisomer of the corresponding cyclobutane derivative (see schematic presentation), the stereo-chemistry of which has been determined unambiguously in the solid state by X-ray crystallography to be syn-anti-syn.

KW - Photochemistry

KW - Pseudorotaxanes

KW - Self-assembly

KW - Solid-state reactions

KW - Template synthesis

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ER -

Host-guest chemistry aids and abets a stereospecific photodimerization in the solid state

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

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