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从2,5-二甲酰基-1,4-二氢吡咯并[3,2-]吡咯到四极、中心对称的双光子吸收A-D-A型染料。

From 2,5-Diformyl-1,4-dihydropyrrolo[3,2-]pyrroles to Quadrupolar, Centrosymmetric Two-Photon-Absorbing A-D-A Dyes.

作者信息

Kowalczyk Paweł, Tasior Mariusz, Ozaki Shuhei, Kamada Kenji, Gryko Daniel T

机构信息

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

NMRI, National Institute of Advanced Industrial Science and Technology (AIST), Ikeda, Osaka 563-8577, Japan.

出版信息

Org Lett. 2022 Apr 8;24(13):2551-2555. doi: 10.1021/acs.orglett.2c00718. Epub 2022 Mar 28.

DOI:10.1021/acs.orglett.2c00718
PMID:35343707
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9003575/
Abstract

An original approach has been developed for the insertion of formyl substituents at positions 2 and 5 of 1,4-dihydropyrrolo[3,2-]pyrroles by conversion of thiazol-2-yl substituents. The synthetic utility of these formyl groups was investigated, and a series of centrosymmetric A-π-D-π-A frameworks were constructed. The two-photon absorption of the quadrupolar pyrrolo[3,2-]pyrrole possessing two dicyanovinylidene flanking groups is attributed to an S → (S) → S transition which has a large TPA cross-section (1300 GM) for a molecule of this size.

摘要

通过噻唑-2-基取代基的转化，已开发出一种在1,4-二氢吡咯并[3,2-]吡咯的2位和5位引入甲酰基取代基的原创方法。研究了这些甲酰基的合成效用，并构建了一系列中心对称的A-π-D-π-A骨架。具有两个二氰基亚乙烯基侧翼基团的四极吡咯并[3,2-]吡咯的双光子吸收归因于S→(S)→S跃迁，对于这种尺寸的分子，该跃迁具有较大的双光子吸收截面（1300 GM）。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/219b/9003575/97b3f58d9771/ol2c00718_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/219b/9003575/b93c3bccb44b/ol2c00718_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/219b/9003575/473149751670/ol2c00718_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/219b/9003575/c5a49922e189/ol2c00718_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/219b/9003575/97b3f58d9771/ol2c00718_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/219b/9003575/b93c3bccb44b/ol2c00718_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/219b/9003575/473149751670/ol2c00718_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/219b/9003575/c5a49922e189/ol2c00718_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/219b/9003575/97b3f58d9771/ol2c00718_0002.jpg

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