Near-infrared absorbing hydrogen-bonded dithioketopyrrolopyrrole (DTPP) n-type semiconductors

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216305%3A26310%2F21%3APU141958" target="_blank" >RIV/00216305:26310/21:PU141958 - isvavai.cz</a>

Alternative codes found

RIV/68378271:_____/22:00555817 RIV/00216208:11310/22:10433533

Result on the web

<a href="https://www.sciencedirect.com/science/article/pii/S0143720821007506?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0143720821007506?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.dyepig.2021.109884" target="_blank" >10.1016/j.dyepig.2021.109884</a>

Result language

angličtina

Original language name

Near-infrared absorbing hydrogen-bonded dithioketopyrrolopyrrole (DTPP) n-type semiconductors

Original language description

Optical and semiconducting properties of vacuum-deposited thin films of four hydrogen-bonded pigments were studied. Well-known 1,4-diketo-3,6-diphenyl-pyrrolo-[3,4-c]-pyrrole (Ph-DPP) and 1,4-diketo-3,6-(thiophen-2yl)-pyrrolo-[3,4-c]-pyrrole (Th-DPP) were transformed to their 1,4-dithioketo heteroanalogues (Ph-DTPP and ThDTPP) using Lawesson's reagent. X-ray single crystal structure determination confirmed the presence of CS-HN hydrogen bonds and a similar stack formation in both DTPPs, leading to relatively high decomposition temperatures, about 350 degrees C. According to density functional theory (DFT) calculations, thionation left HOMO (pi-type) level almost unchanged, considerably destabilized non-bonding orbital (n-orbital) localized on thioketo group, and significantly decreased LUMO (pi*-type) energy. Evolution of HOMO and LUMO energies was confirmed by cyclic voltammetry, establishing LUMO energy at -4.5 eV for both DTPPs, while a signature of high-lying n-orbital was detected through n pi* transition in the far-red/near-infrared area of absorption spectra, interpreted with help of time dependent DFT calculations on monomer and stacked dimer geometry. The lowest optical band-gap among the pigments under study was found to be 1.4 eV for Ph-DTPP thin film. Field effect mobilities, determined on a bottom-gate top-contact transistor, show DPPs as p-type and DTPPs as n-type semiconductors. The highest electron mobility mu e = 0.018 cm2 V-1 s- 1 was obtained for Ph-DTPP film in the device with aluminium source and drain electrodes.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2021

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

DYES AND PIGMENTS

ISSN

0143-7208

e-ISSN

1873-3743

Volume of the periodical

197

Issue of the periodical within the volume

1

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

109884-109895

UT code for WoS article

000708571900006

EID of the result in the Scopus database

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