The role of aromatic π-bridges in push–pull-chromophores on the transparency-hyperpolarizability tradeoff

Through-conjugation for a wide range of 1, 8-diamino-4,5-dinitronaphthalenes (N-acylated, N-alkylated, N,N 0 -bridged, N-heterocyclic, and N-deprotonated compounds) was for the first time quantified in solution by means of ultravioletvisible and proton nuclear magnetic resonance spectroscopy and compared with that of the simpler naphthalene and benzene push-pull systems. Surprisingly, an extent of conjugation in 1,8-diamino-4-nitro-and 1,8-diamino-4,5dinitronaphthalenes measured in dimethyl sulfoxide is commensurable. On the whole, the repulsive peri-interactions between the amino groups in systems with N-alkylated and N-deprotonated amino groups are more favorable for an effective D-p-A charge transfer than in N,N 0 -bridged compounds (perimidines, 2,3-dihydroperimidines and perimidin-2-ones). The best electron donors from peri-positions are pyrrolidin-1-yl and methylamido groups. The conclusions obtained from solution studies were deepened by solid-state X-ray experiments for a number of push-pull naphthalenes, including 6,7-dinitroperimidine N-anion and two representatives of 4,5-diaminonaphthalene-1,8-dicarbaldehydes. In particular, they helped to trace changes in the bond order redistribution and twisting of the naphthalene core. The latter reaches a record value of 27 for 4,5-dinitro-1,8-di(pyrrolidin-1-yl)naphthalene.

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To what extent can a conjugation between two pairs of peri‐nitro and peri‐amino groups be realized through the naphthalene core?

Ozeryanskii

Filatova

Пожарский

et al. 2013

J of Physical Organic Chem

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A quantitative analysis of intramolecular charge transfer contribution to polarizability responses in donor-π-acceptor molecules

Liu

Yang

Chu

et al. 2011

Chemical Physics Letters

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Electro-optic and spectroscopic properties of push–pull-chromophores with non-aromatic π-bridges

Rinderspacher

2013

Chemical Physics Letters

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The role of aromatic π-bridges in push–pull-chromophores on the transparency-hyperpolarizability tradeoff

Cited by 8 publications

References 35 publications

To what extent can a conjugation between two pairs of peri‐nitro and peri‐amino groups be realized through the naphthalene core?

To what extent can a conjugation between two pairs of peri‐nitro and peri‐amino groups be realized through the naphthalene core?

A quantitative analysis of intramolecular charge transfer contribution to polarizability responses in donor-π-acceptor molecules

Electro-optic and spectroscopic properties of push–pull-chromophores with non-aromatic π-bridges

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