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T‐Shaped (Donor–π–) 2 Acceptor–π–Donor Push–Pull Systems Based on Indan‐1,3‐dione
Author(s) -
Solanke Parmeshwar,
Bureš Filip,
Pytela Oldřich,
Klikar Milan,
Mikysek Tomáš,
Mager Loic,
Barsella Alberto,
Růžičková Zdeňka
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500525
Subject(s) - chemistry , thiophene , molecule , acceptor , ring (chemistry) , benzene , crystallography , differential scanning calorimetry , electron donor , stereochemistry , organic chemistry , catalysis , physics , thermodynamics , condensed matter physics
Sixteen model (donor–π–) 2 acceptor–π–donor [(D–π–) 2 A–π–D] molecules with an extraordinary T‐shaped arrangement were designed and synthesized. Indan‐1,3‐dione was employed as a central acceptor with electron donors linked at the C‐2, C‐4, and C‐7 positions. These push–pull molecules represent a first systematic modification of an indan‐1,3‐dione‐fused benzene ring. The structures and properties of all target molecules were investigated by X‐ray analysis, electrochemistry, UV/Vis absorption spectroscopy, differential scanning calorimetry, electric‐field‐induced second‐harmonic generation (EFISHG) studies, and DFT calculations. A thorough evaluation of all of the gathered data has been performed, and structure–property relationships were evaluated. Electron donors attached at the C‐2 position through π systems of various lengths affect the studied properties most significantly. The side donors at C‐4 and C‐7 can be described as auxiliary and do not dominate the observed properties. However, thiophene is a more efficient donor than N , N ‐dimethylaniline in this respect. Hence, indan‐1,3‐dione bearing a piperidylthiophene donor connected through a propenylidene spacer at C‐2 completed with two side thiophen‐2‐ylethynyl branches at C‐4 and C‐7 showed the highest figure of merit among the studied properties.