Perilen Diimid Türevlerinin Uyarılmış Hal Özelliklerine İmid İkamelerinin Etkisi

Year 2022, Volume: 17 Issue: 1, 11 - 21, 20.03.2022

Erkan Aksoy Andrew Danos Chunyong Li Andrew Monkman Canan Varlıklı

https://doi.org/10.55525/tjst.952823

Abstract

Fluoresant malzemelerin katı hal optik özellikleri organik ışık yayan diyotlar, frekans dönüştürücü veya ışıyan güneş yoğunlaştırıcıları gibi birçok optik ve elektronik fotonik aygıtlar için önemlidir. Perilen diimidler (PDIs) bu fotonik aygıt uygulamalarında yer bulan en popüler organik yarı iletkenlerden birini temsil etmektedir. Bu çalışmada, biri dallı alkil zinciri (2-etilheksil, 2-EH) diğeri aromatik (diizopropilfenil, DIA) yer değiştirebilen grup içeren iki dibromlu PDI'nin (DiBrPDIs) fotofiziksel özellikleri karşılaştırmalı olarak incelenmiştir. Soğurma ve fotolüminesans (PL), yaşam ömürü ve fotolüminesans kuantum veriminin (PLQY) yanı sıra, foto-uyarımlı absorpsiyon özellikleri de (PIA) fs-geçici soğurma spektroskopisi ile incelenmiştir. Aynı π konjuge sistemleri nedeniyle, DiBrPDI-DIA ve DiBrPDI-2EH, çözelti fazında (λabs:527 nm ve λPL:552 nm) özdeş soğurma ve PL davranışlarına sahiptir. Ancak, aynı koşullarda hazırlanan filmlerde DiBrPDI-DIA (λPL-DIA:596 nm; PLQY:73.4%), DiBrPDI-2EH'den (λPL-2EH:649 nm; PLQY:36.7%) daha yüksek bir PLQY ile daha kısa dalgaboyunda bir PL spektruma sahiptir. Chem3D pro yazılımı kullanılarak gerçekleştirilen 3 boyutlu hesaplamalar, bu durumun hacimli DIA grupların perilen halkaları arasındaki mesafeyi artırmasından kaynakladığını göstermiştir.

Keywords

Katı hal fluoresans, perilen diimid, fs-geçici soğurma spektroskopi, sterik koruyucu

Project Number

BIDEB-2214-A (Appl. # 1059B141800476) ve TUBITAK #119F031

The Effect of Imide Substituents on the Excited State Properties of Perylene Diimide Derivatives

Abstract

Solid state optical properties of fluorescent materials are important for many optical and electronic photonic devices such as organic light emitting diodes, frequency down-converters or luminescent solar concentrators. Perylene diimides (PDIs) represent one of the most popular organic semiconductors which find application in those phonic device applications. In this study, photophysical properties of two dibrominated PDI (DiBrPDIs), one of which contains a branched alkyl chain (2-ethylhexyl, 2-EH) and the other has an aromatic substituent (diisopropylphenyl, DIA) at the imide positions are comparatively studied. Besides their absorption and photoluminescence, lifetime and photoluminescence quantum yield (PLQY), photoinduced absorption properties (PIA) were also examined by fs-transient absorption spectroscopy. Due to their the same π conjugated system, DiBrPDI-DIA and DiBrPDI-2EH exhibited identical absorption and photoluminescence (PL) spectra in solution phase (λabs:527 nm and λPL:552 nm). However, in their film phases which were prepared at the same conditions, DiBrPDI-DIA (λPL-DIA:596 nm; PLQY:73.4%) presented a shorter PL wavelength with a higher PLQY than that of DiBrPDI-2EH (λPL-2EH:649 nm; PLQY:36.7%). 3-D investigations performed by using Chem3D pro software addressed the higher intermolecular distance between the perylene rings induced by the bulky DIA groups, as the main reason of this difference.

Keywords

Solid state fluorescence, perylene diimide, fs-transient absorption spectroscopy, steric shielding

Supporting Institution

Türkiye Bilimsel ve Teknolojik Araştırma Kurumu (TUBITAK) ve TUBITAK-Bilim İnsanı Destekleme Daire Başkanlığı (BIDEB) (2214A)

Project Number

BIDEB-2214-A (Appl. # 1059B141800476) ve TUBITAK #119F031

Thanks

EA thanks The Scientific and Technological Research Council of Turkey (TUBITAK) BIDEB-2214-A (Appl. # 1059B141800476) who supported this research financially – for ultrafast pump probe transient absorption spectroscopy in Durham. EA and CV also thank the project support funds of TUBITAK grant #119F031 for financial support of the synthesis, structural and optical characterizations of DiBrPDIs.

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