Diphenylaminocarbazoles by 1,8-functionalization of carbazole: Materials and application to phosphorescent organic light-emitting diodes

Ameen, Shahid; Lee, Seul Bee; Yoon, Sung Cheol; Lee, Jaemin; Lee, Changjin

doi:10.1016/j.dyepig.2015.08.027

Cited by 20 publications

(11 citation statements)

References 51 publications

(38 reference statements)

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“…Karbazoller iyi optik özelliklere, düşük redoks potansiyeline ve yüksek kimyasal stabiliteye sahiptir. Bu nedenle, sustitüye ve oligo/polikarbazoller, organik alan etkili transistör ve organik güneş pilleri gibi aygıtlarda kullanılmıştır [8,9]. Ayrıca karbazol ve türevleri, iyi fotovoltaik performans göstermesi, boşluk transferinde etkili ve geniş bant aralığına sahip olmaları nedeniyle boya duyarlı güneş pillerinde (BDGP) boyaları hassaslaştırmak için yaygın olarak kullanılan donörlerdendir [10,11].…”

Section: Introductionunclassified

Boya Duyarlı Güneş Pillleri için Karbazol Tiyofen Türevli Moleküllerin Sentezi ve Karakterizasyonu

Erden

Görgün

2021

Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi

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Özet: Bu çalışmada ilk olarak, karbazol başlangıç maddesi kullanılarak, N-bromo süksinimid ile bromlama reaksiyonu yapılmış ve 3,6-dibromokarbazol (II) elde edilmiştir. Daha sonra, 3,6dibromokarbazol (II) ve oktil bromür kullanılarak alkilleme reaksiyonu yapılmış ve 3,6dibromo-9-oktilkarbazol (III) elde edilmiştir. Son aşamada ise Suzuki-Miyaura çapraz kenetlenme reaksiyonu ile farklı arilboronik asitler kullanılarak, D-A sistemine uygun literatürde olmayan yeni karbazol türevli maddeler 3,6-bis-benzo[b]tiyofen-2-il-9-oktil-9Hkarbazol (IV) ve 3,6-bis-(5-kloro-tiyofen-2-il)-9-oktilkarbazol (V) sentezlenmiştir. Sentezlenen bu maddelerin yapıları 1 H-NMR ve 13 C-NMR spektroskopik yöntemler kullanılarak aydınlatılmıştır. Ayrıca yeni sentezlenen IV ve V numaralı moleküllerin, boya duyarlı güneş pillerinde (BDGP) boya malzemesi olarak kullanımı da araştırılmıştır. Bunun için BDGP-IV ve BDGP-V kodlu piller hazırlanıp, elektriksel karakterizasyonları yapılmıştır.

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Section: Introductionunclassified

Boya Duyarlı Güneş Pillleri için Karbazol Tiyofen Türevli Moleküllerin Sentezi ve Karakterizasyonu

Erden

Görgün

2021

Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi

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“…[1,11] Yet, few derivatives featuring chromophores on C1 and C8-positions (ortho-to carbazole nitrogen) are registered which possess alkyl units at C3 and C6À positions. [12] Recently, multi-functionalized (tri-substituted at C1, C3 and C6 and tetrasubstituted at C1, C3, C6 and C8) carbazoles are reported to display decent OLED performance. [13][14][15][16] However, tri-substituted at C2, C3 and C7 and tetra-substituted at C2, C3, C6 and C7 are ill explored due to the tedious synthetic protocols.…”

Section: Introductionmentioning

confidence: 99%

Fine‐Tuning the Physicochemical and Electroluminescence Properties of Multiply‐Substituted Bipolar Carbazoles by Functional Group Juggling

et al. 2020

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The nature of chromophores often plays a decisive role in imparting properties to functional materials. In this work, we demonstrate that the position of the chromophoric unit on the carbazole core is crucial to tune the photophysical and electroluminescence properties. A series of bipolar compounds featuring carbazole donor and cyano acceptor groups are used as model compounds to evaluate the proposed hypothesis. It is revealed that the conjugation connectivity and chromophore density significantly affects the functional properties of the dyes. A compound featuring carbazole on the C2 and C7 positions of a carbazole core displayed a more bathochromic absorption band than its structural isomer with carbazole on C1 and C8 positions. A major change in emission properties is achieved on changing the position of the carbazole and cyano units on carbazole nucleus. The emission spectra of the dyes are sensitive to solvent polarity and displayed positive solvatochromism attributable to the photoinduced charge transfer from the peripheral carbazole donor to the cyano acceptor. They are demonstrated as dopant emitters in solution-processed multilayer organic light emitting devices and exhibited deep-blue or sky-blue emission with CIE coordinates varying in the range: 0.14 � x � 0.20, 0.07 � y � 0.16. A compound containing a carbazole donor on C3 and C6 and a cyano acceptor on C2 and C7 positions of the carbazole core exhibited the best performance in an OLED with a maximum external quantum efficiency of 3.4 %.

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“…Moreover, 1-C to 8-C positions can be easily functionalized with suitable groups, opening the route to the synthesis of many carbazole-based derivatives. [28,29] 9H-Carbazole and its derivatives have been extensively used as electron donating (D) units in π-conjugated small molecules and polymers. [30,31] On the other hand, 2,2':6',2''-terpyridine and its derivatives are readily accessible molecules widely used in organic and supramolecular chemistry, due to their electron accepting (A) character and, most remarkably, to the ability of serving as tridentate ligands, [32] also largely used in photoactive polynuclear metal complexes.…”

Section: Introductionmentioning

confidence: 99%

“…The presence of a nitrogen atom in the 9 position enables easy coupling with other functional groups, without altering the electronic and photophysical properties of the molecule. Moreover, 1‐C to 8‐C positions can be easily functionalized with suitable groups, opening the route to the synthesis of many carbazole‐based derivatives …”

Section: Introductionmentioning

confidence: 99%

Carbazole‐Terpyridine Donor‐Acceptor Dyads with Rigid π‐Conjugated Bridges

et al. 2019

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A series of molecules in which 9H‐carbazole (electron donor, D) and 2,2′:6′,2′′‐terpyridine (electron acceptor, A) are connected through rigid π‐conjugated bridges (D‐π‐A systems) have been synthesized and their photophysical properties examined in detail, with the support of DFT calculations. The bridges are made of different sequences of ethynylene, phenylene, and anthracene groups. The synthetic strategies involve condensation of 2‐acetylpyridine with the aromatic aldehyde moiety on different functionalized π‐conjugated bridges and couplings with carbazole derivatives. The system incorporating anthracene in the bridge shows the typical absorption and emission fingerprints of this polycyclic hydrocarbon. The other systems have HOMOs and LUMOs centred, respectively, over the carbazole and the bridge and exhibit solvatochromic charge‐transfer (CT) luminescence with high photoluminescence yield up to 70 %, except when an ethynylene unit is directly attached to the carbazole ring, due to a trans‐bent non‐emissive π–σ* excited state.

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Diphenylaminocarbazoles by 1,8-functionalization of carbazole: Materials and application to phosphorescent organic light-emitting diodes

Cited by 20 publications

References 51 publications

Boya Duyarlı Güneş Pillleri için Karbazol Tiyofen Türevli Moleküllerin Sentezi ve Karakterizasyonu

Boya Duyarlı Güneş Pillleri için Karbazol Tiyofen Türevli Moleküllerin Sentezi ve Karakterizasyonu

Fine‐Tuning the Physicochemical and Electroluminescence Properties of Multiply‐Substituted Bipolar Carbazoles by Functional Group Juggling

Carbazole‐Terpyridine Donor‐Acceptor Dyads with Rigid π‐Conjugated Bridges

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