Oligothiophene-Functionalized Benzene and Tetrathienoanthracene: Effect of Enhanced -Conjugation on Optoelectronic Properties, Self-Assembly and Device Performance

被引：14

作者：

Leitch, Alicea A. ^{[1
,2
]}

Stobo, Kimberly A. ^{[1
,2
]}

Hussain, Bashir ^{[1
,2
]}

Ghoussoub, Mireille ^{[3
]}

Ebrahimi-Takalloo, Saeedeh ^{[3
]}

Servati, Peyman ^{[3
]}

Korobkov, Ilia ^{[1
]}

Brusso, Jaclyn L. ^{[1
,2
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

[2] Univ Ottawa, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada

[3] Univ British Columbia, Dept Elect & Comp Engn, Vancouver, BC V6T 1Z4, Canada

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 26期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Semiconductors; Pi interactions; Substituent effects; Molecular devices; Conducting materials; CHARGE-TRANSPORT; ELECTRONIC-PROPERTIES; CRYSTAL-STRUCTURES; TRANSISTORS; SEMICONDUCTORS; SYSTEMS; DESIGN; ACENES;

D O I：

10.1002/ejoc.201300731

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The versatility of fourfold Stille coupling to afford oligothiophene-functionalized tetrathienoanthracene (TTA) and benzene derivatives is described. The influence of the larger, more rigid TTA core on the electronic and structural properties was investigated. Comparative optical and electrochemical studies demonstrate a diminishing HOMO-LUMO gap as the length of the oligothiophene chain increases, with the rigid TTA compounds exhibiting lower energy gaps than the more flexible benzene analogues. X-ray crystallography studies reveal that the thiophene-substituted TTA structure consists of slipped -stacks with several close intrastack - interactions; no close contacts are observed for the benzene derivative due to twisting of the thiophene ligands out of plane. Consequently, the molecules in the benzene analogue are isolated from their neighbours. The thiophene and bithiophene functionalised TTA compounds were fabricated into OTFT devices in bottom-contact configuration and exhibited mobilities of ca. 10(-4) cm(2)V(-1)s(-1) and on/off ratios of more than four orders of magnitude.

引用

页码：5854 / 5863

页数：10

共 56 条

[1]

[Anonymous], APEX SOFTW SUIT V 20

[2]

Anthony J. E., 2008, ANGEW CHEM, V120, P460

[3] The larger acenes: Versatile organic semiconductors [J].

Anthony, John E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483

[4] Functionalized acenes and heteroacenes for organic electronics [J].

Anthony, John E. .

CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048

[5] Oligothiophene S,S-dioxides.: Synthesis and electronic properties in relation to the parent oligothiophenes [J].

Barbarella, G ;

Favaretto, L ;

Sotgiu, G ;

Zambianchi, M ;

Antolini, L ;

Pudova, O ;

Bongini, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5497-5506

[6] Oligothiophenes end-capped by nitriles. Preparation and crystal structures of alpha,omega-dicyanooligothiophenes NC(C4H2S)(n)CN (n=3-6) [J].

Barclay, TM ;

Cordes, AW ;

MacKinnon, CD ;

Oakley, RT ;

Reed, RW .

CHEMISTRY OF MATERIALS, 1997, 9 (04) :981-990

[7] Synthesis, Crystal Structures, and Electronic Properties of Nonlinear Fused Thienoacene Semiconductors [J].

Black, Hayden T. ;

Liu, Shubin ;

Ashby, Valerie Sheares .

ORGANIC LETTERS, 2011, 13 (24) :6492-6495

[8]

Blum M.-C., 2005, ANGEW CHEM, V117, P5468

[9] Conservation of chirality in a hierarchical supramolecular self-assembled structure with pentagonal symmetry [J].

Blüm, MC ;

Cavar, E ;

Pivetta, M ;

Patthey, F ;

Schneider, WD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5334-5337

[10] ELECTROCHEMICAL EVIDENCE FOR THE EXISTENCE OF 3 STABLE OXIDATION-STATES FOR HETEROCYCLES OF THE TYPE-X-C6H4-CN2E2 (E=S, SE) - X-RAY CRYSTAL-STRUCTURE OF THE DIMER WITH X=CL, E=S [J].

BOERE, RT ;

MOOCK, KH ;

PARVEZ, M .

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1994, 620 (09) :1589-1598

← 1 2 3 4 5 6 →