Synthesis and Photophysics of Ambipolar Fluoren-9-ylidene Malononitrile Derivatives

被引：48

作者：

Estrada, Leandro A. ^{[1
]}

Neckers, Douglas C. ^{[1
]}

机构：

[1] Bowling Green State Univ, Ctr Photochem Sci, Bowling Green, OH 43403 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 21期

关键词：

INTRAMOLECULAR CHARGE-TRANSFER; LIGHT-EMITTING-DIODES; 2-PHOTON ABSORPTION; ELECTRON-ACCEPTORS; FLUORENE SERIES; TRIPLET-ENERGY; COVALENT BONDS; HOST MATERIALS; BASIS-SET; MOLECULES;

D O I：

10.1021/jo901869g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient synthesis of ambipolar 2,7- and 3,6-disubstituted fluoren-9-ylidene malononitrile derivatives (4 and 9) is described. Structure-activity relationships depend on the position of substitution. Population of the S-1 excited state in the 2,7-disubstituted FM derivatives is achieved via higher states, as evidenced from the UV-vis absorption and emission spectra. The results are supported by TDDFT calculations. Charge transfer states were the main deactivation path of the excited states of ambipolar 9b in polar solvents, as evidenced by fluorescence spectroscopy

引用

页码：8484 / 8487

页数：4

共 57 条

[1]

Albaugh P. A., 2007, US Pat., Patent No. [US/20070066573, 20070066573]

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3]

[Anonymous], CURRENT TRENDS POLYM

[4] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[5] Two-photon absorption cross section determination for fluorene derivatives: Analysis of the methodology and elucidation of the origin of the absorption processes [J].

Belfield, Kevin D. ;

Bondar, Mykhailo V. ;

Hernandezt, Florencio E. ;

Przhonska, Olga V. ;

Yao, Sheng .

JOURNAL OF PHYSICAL CHEMISTRY B, 2007, 111 (44) :12723-12729

[6] Two-Photon Absorption Properties of New Fluorene-Based Singlet Oxygen Photosensitizers [J].

Belfield, Kevin D. ;

Bondar, Mykhailo V. ;

Hernandez, Florencio E. ;

Masunov, Artem E. ;

Mikhailov, Ivan A. ;

Morales, Alma R. ;

Przhonska, Olga V. ;

Yao, Sheng .

JOURNAL OF PHYSICAL CHEMISTRY C, 2009, 113 (11) :4706-4711

[7] Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics [J].

Bendikov, M ;

Wudl, F ;

Perepichka, DF .

CHEMICAL REVIEWS, 2004, 104 (11) :4891-4945

[8] QUINONE STUDIES .I. EVIDENCE FOR NEW TYPE OF SUBSTITUTION REACTION OF PHENANTHRENE-9,10-QUINONE DERIVATIVES [J].

BHATT, MV .

TETRAHEDRON, 1964, 20 (04) :803-+

[9] Photophysics of arylene and heteroaryleneethinylenes [J].

Birckner, E ;

Grummt, UW ;

Göller, AH ;

Pautzsch, T ;

Egbe, DAM ;

Al-Higari, M ;

Klemm, E .

JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (45) :10307-10315

[10] Carbazole compounds as host materials for triplet emitters in organic light-emitting diodes:: Tuning the HOMO level without influencing the triplet energy in small molecules [J].

Brunner, K ;

van Dijken, A ;

Börner, H ;

Bastiaansen, JJAM ;

Kiggen, NMM ;

Langeveld, BMW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :6035-6042

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