1,2,3-Triazole-Diketopyrrolopyrrole Derivatives with Tunable Solubility and Intermolecular Interactions

Angela Punzi; Eliana Maiorano; Francesca Nicoletta; Davide Blasi; Antonio Ardizzone; Nora Ventosa; Imma Ratera; Jaume Veciana; Gianluca Maria Farinola

doi:10.1002/ejoc.201600120

1,2,3-Triazole-Diketopyrrolopyrrole Derivatives with Tunable Solubility and Intermolecular Interactions

Angela Punzi, Eliana Maiorano, Francesca Nicoletta, Davide Blasi, Antonio Ardizzone, Nora Ventosa, Imma Ratera, Jaume Veciana, Gianluca Maria Farinola

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

19 Citations (Scopus)

Abstract

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 1,2,3-Triazole rings bearing hydrophobic aliphatic or hydrophilic oligoether chains were easily introduced at the two ends of the conjugated skeleton of bisthiophene-diketopyrrolopyrrole (TDPP) derivatives by simple click cycloaddition reactions. The combination of side chains with different structures and polarities on the triazole rings with the side chains on the N-atoms of the lactam groups of the TDPP moiety enabled the solubility and the solid-state spectroscopic properties of the resulting conjugated molecules to be tuned. Formation of nanostructured aggregates and dependence of their spectroscopic behavior on the substitution pattern were investigated.

Original language	English
Pages (from-to)	2617-2627
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	15
DOIs	https://doi.org/10.1002/ejoc.201600120
Publication status	Published - 1 May 2016

Keywords

Azides
Click chemistry
Conjugation
Dyes/Pigments
Nitrogen heterocycles

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title = "1,2,3-Triazole-Diketopyrrolopyrrole Derivatives with Tunable Solubility and Intermolecular Interactions",

abstract = "{\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 1,2,3-Triazole rings bearing hydrophobic aliphatic or hydrophilic oligoether chains were easily introduced at the two ends of the conjugated skeleton of bisthiophene-diketopyrrolopyrrole (TDPP) derivatives by simple click cycloaddition reactions. The combination of side chains with different structures and polarities on the triazole rings with the side chains on the N-atoms of the lactam groups of the TDPP moiety enabled the solubility and the solid-state spectroscopic properties of the resulting conjugated molecules to be tuned. Formation of nanostructured aggregates and dependence of their spectroscopic behavior on the substitution pattern were investigated.",

keywords = "Azides, Click chemistry, Conjugation, Dyes/Pigments, Nitrogen heterocycles",

author = "Angela Punzi and Eliana Maiorano and Francesca Nicoletta and Davide Blasi and Antonio Ardizzone and Nora Ventosa and Imma Ratera and Jaume Veciana and Farinola, {Gianluca Maria}",

year = "2016",

month = may,

day = "1",

doi = "10.1002/ejoc.201600120",

language = "English",

volume = "2016",

pages = "2617--2627",

number = "15",

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1,2,3-Triazole-Diketopyrrolopyrrole Derivatives with Tunable Solubility and Intermolecular Interactions. / Punzi, Angela; Maiorano, Eliana; Nicoletta, Francesca; Blasi, Davide; Ardizzone, Antonio; Ventosa, Nora; Ratera, Imma; Veciana, Jaume; Farinola, Gianluca Maria.

In: European Journal of Organic Chemistry, Vol. 2016, No. 15, 01.05.2016, p. 2617-2627.

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

TY - JOUR

T1 - 1,2,3-Triazole-Diketopyrrolopyrrole Derivatives with Tunable Solubility and Intermolecular Interactions

AU - Punzi, Angela

AU - Maiorano, Eliana

AU - Nicoletta, Francesca

AU - Blasi, Davide

AU - Ardizzone, Antonio

AU - Ventosa, Nora

AU - Ratera, Imma

AU - Veciana, Jaume

AU - Farinola, Gianluca Maria

PY - 2016/5/1

Y1 - 2016/5/1

N2 - © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 1,2,3-Triazole rings bearing hydrophobic aliphatic or hydrophilic oligoether chains were easily introduced at the two ends of the conjugated skeleton of bisthiophene-diketopyrrolopyrrole (TDPP) derivatives by simple click cycloaddition reactions. The combination of side chains with different structures and polarities on the triazole rings with the side chains on the N-atoms of the lactam groups of the TDPP moiety enabled the solubility and the solid-state spectroscopic properties of the resulting conjugated molecules to be tuned. Formation of nanostructured aggregates and dependence of their spectroscopic behavior on the substitution pattern were investigated.

AB - © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 1,2,3-Triazole rings bearing hydrophobic aliphatic or hydrophilic oligoether chains were easily introduced at the two ends of the conjugated skeleton of bisthiophene-diketopyrrolopyrrole (TDPP) derivatives by simple click cycloaddition reactions. The combination of side chains with different structures and polarities on the triazole rings with the side chains on the N-atoms of the lactam groups of the TDPP moiety enabled the solubility and the solid-state spectroscopic properties of the resulting conjugated molecules to be tuned. Formation of nanostructured aggregates and dependence of their spectroscopic behavior on the substitution pattern were investigated.

KW - Azides

KW - Click chemistry

KW - Conjugation

KW - Dyes/Pigments

KW - Nitrogen heterocycles

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DO - 10.1002/ejoc.201600120

M3 - Article

VL - 2016

SP - 2617

EP - 2627

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ER -