Tunable Properties of Nature-Inspired <i>N</i>,<i>N</i>′-Alkylated Riboflavin Semiconductors

A series of novel soluble nature-inspired flavin derivatives substituted with short butyl and bulky ethyl-adamantyl alkyl groups was prepared via simple and straightforward synthetic approach with moderate to good yields. The comprehensive characterization of the materials, to assess their applicati...

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Main Authors: Jan Richtar, Lucia Ivanova, Dong Ryeol Whang, Cigdem Yumusak, Dominik Wielend, Martin Weiter, Markus Clark Scharber, Alexander Kovalenko, Niyazi Serdar Sariciftci, Jozef Krajcovic
Format: Article
Language:English
Published: MDPI AG 2020-12-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/26/1/27
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author Jan Richtar
Lucia Ivanova
Dong Ryeol Whang
Cigdem Yumusak
Dominik Wielend
Martin Weiter
Markus Clark Scharber
Alexander Kovalenko
Niyazi Serdar Sariciftci
Jozef Krajcovic
author_facet Jan Richtar
Lucia Ivanova
Dong Ryeol Whang
Cigdem Yumusak
Dominik Wielend
Martin Weiter
Markus Clark Scharber
Alexander Kovalenko
Niyazi Serdar Sariciftci
Jozef Krajcovic
author_sort Jan Richtar
collection DOAJ
description A series of novel soluble nature-inspired flavin derivatives substituted with short butyl and bulky ethyl-adamantyl alkyl groups was prepared via simple and straightforward synthetic approach with moderate to good yields. The comprehensive characterization of the materials, to assess their application potential, has demonstrated that the modification of the conjugated flavin core enables delicate tuning of the absorption and emission properties, optical bandgap, frontier molecular orbital energies, melting points, and thermal stability. Moreover, the thin films prepared thereof exhibit smooth and homogeneous morphology with generally high stability over time.
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spelling doaj.art-748b89a193c141ec9c6e16ff045d06652023-11-21T02:11:57ZengMDPI AGMolecules1420-30492020-12-012612710.3390/molecules26010027Tunable Properties of Nature-Inspired <i>N</i>,<i>N</i>′-Alkylated Riboflavin SemiconductorsJan Richtar0Lucia Ivanova1Dong Ryeol Whang2Cigdem Yumusak3Dominik Wielend4Martin Weiter5Markus Clark Scharber6Alexander Kovalenko7Niyazi Serdar Sariciftci8Jozef Krajcovic9Materials Research Centre, Faculty of Chemistry, Brno University of Technology, Purkyňova 118, 612 00 Brno, Czech RepublicMaterials Research Centre, Faculty of Chemistry, Brno University of Technology, Purkyňova 118, 612 00 Brno, Czech RepublicLinz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, AustriaLinz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, AustriaLinz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, AustriaMaterials Research Centre, Faculty of Chemistry, Brno University of Technology, Purkyňova 118, 612 00 Brno, Czech RepublicLinz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, AustriaMaterials Research Centre, Faculty of Chemistry, Brno University of Technology, Purkyňova 118, 612 00 Brno, Czech RepublicLinz Institute for Organic Solar Cells (LIOS), Physical Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, AustriaMaterials Research Centre, Faculty of Chemistry, Brno University of Technology, Purkyňova 118, 612 00 Brno, Czech RepublicA series of novel soluble nature-inspired flavin derivatives substituted with short butyl and bulky ethyl-adamantyl alkyl groups was prepared via simple and straightforward synthetic approach with moderate to good yields. The comprehensive characterization of the materials, to assess their application potential, has demonstrated that the modification of the conjugated flavin core enables delicate tuning of the absorption and emission properties, optical bandgap, frontier molecular orbital energies, melting points, and thermal stability. Moreover, the thin films prepared thereof exhibit smooth and homogeneous morphology with generally high stability over time.https://www.mdpi.com/1420-3049/26/1/27soluble alkylated flavinsbio-inspired materialsorganic electronicsside-chain engineeringfused-ring systemsriboflavin
spellingShingle Jan Richtar
Lucia Ivanova
Dong Ryeol Whang
Cigdem Yumusak
Dominik Wielend
Martin Weiter
Markus Clark Scharber
Alexander Kovalenko
Niyazi Serdar Sariciftci
Jozef Krajcovic
Tunable Properties of Nature-Inspired <i>N</i>,<i>N</i>′-Alkylated Riboflavin Semiconductors
Molecules
soluble alkylated flavins
bio-inspired materials
organic electronics
side-chain engineering
fused-ring systems
riboflavin
title Tunable Properties of Nature-Inspired <i>N</i>,<i>N</i>′-Alkylated Riboflavin Semiconductors
title_full Tunable Properties of Nature-Inspired <i>N</i>,<i>N</i>′-Alkylated Riboflavin Semiconductors
title_fullStr Tunable Properties of Nature-Inspired <i>N</i>,<i>N</i>′-Alkylated Riboflavin Semiconductors
title_full_unstemmed Tunable Properties of Nature-Inspired <i>N</i>,<i>N</i>′-Alkylated Riboflavin Semiconductors
title_short Tunable Properties of Nature-Inspired <i>N</i>,<i>N</i>′-Alkylated Riboflavin Semiconductors
title_sort tunable properties of nature inspired i n i i n i alkylated riboflavin semiconductors
topic soluble alkylated flavins
bio-inspired materials
organic electronics
side-chain engineering
fused-ring systems
riboflavin
url https://www.mdpi.com/1420-3049/26/1/27
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