The indanone N-H type excited-state intramolecular proton transfer (ESIPT); the observation of a mechanically induced ESIPT reaction

We report the design and synthesis of indanone derivatives 1-4 with RR′N-H O&z.dbd;C intramolecular hydrogen bonds, in which ESIPT takes place and its dynamics and thermodynamics correlate with H-bond strength, facilitated by electron-withdrawing R′ groups. Compound 4 (R′ = COCF 3 ) shows mechan...

Full description

Saved in:
Bibliographic Details
Published inPhysical chemistry chemical physics : PCCP Vol. 26; no. 4; pp. 25767 - 25771
Main Authors You, Jhu-Jyun, Lin, Yan-Ding, Hsu, Chao-Hsien, Hu, Jiun-Wei, Tsai, Ying-Yi, Qu, Hao-Ting, Chen, Kew-Yu, Chou, Pi-Tai
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 17.10.2024
Subjects
Bonding strength
Chemical synthesis
Hydrogen bonds
Online AccessGet full text
ISSN1463-9076
1463-9084
1463-9084
DOI10.1039/d4cp02862g

Cover

More Information
Summary:We report the design and synthesis of indanone derivatives 1-4 with RR′N-H O&z.dbd;C intramolecular hydrogen bonds, in which ESIPT takes place and its dynamics and thermodynamics correlate with H-bond strength, facilitated by electron-withdrawing R′ groups. Compound 4 (R′ = COCF 3 ) shows mechanically induced ESIPT for the first time, where -CF 3 HN- interaction plays a key role in the non-centrosymmetric crystal packing. We designed and synthesized indanone derivatives with ESIPT, correlated to H-bond strength. Compound 4 shows mechanically induced ESIPT for the first time, with -CF 3 -HN- interactions crucial for non-centrosymmetric crystal packing.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
2371431-2371433
https://doi.org/10.1039/d4cp02862g
and
2375635
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
content type line 23
ISSN:1463-9076
1463-9084
1463-9084
DOI:10.1039/d4cp02862g