Comparative study of electron conduction in azulene and naphthalene

Dutta, Sudipta; Lakshmi, S.; Pati, Swapan K.

doi:10.1007/s12034-008-0055-8

Cited by 21 publications

(27 citation statements)

References 27 publications

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“…The calculations for current-voltage characteristics have been performed using nonequilibrium Green's function [18]. All the calculation details are given in [5,12] th e electro n s easily from th e seven -m em b ered rin g to th ē ve-m em b ered rin g, g iv in g th e sy stem a rom atic sta b ility. …”

Section: Electrical Rectificationmentioning

confidence: 99%

Electrical rectification

Dutta

Pati

2009

Reson

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left) Sudipta Dutta is currently pursuing doctoral research in JNCASR, Bangalore. His research interests include quantum many-body theory, ab initio quantum chemistry, electronic structure theory, molecular electronics and hydrogen storage. (right) Swapan K Pati is an associate professor at JNCASR, Bangalore. His research interests include quantum many-body theory, molecular electronics, non-linear optical phenomena, quantum magnetism, generalized charge-transfer mechanisms and hydrogen storage. He is also actively involved in developing new theoretical tools for a holistic understanding of structure property correlations in a whole range of systems from molecules to materials including biological and bio-mimetic systems. O w in g to th e sa tu ra tio n o f th e e ± c ie n c y o f silic o n d e v ic e s in e le c tro n ic s in d u stry , m o le c u la r e le c tr o n ic s h a s g a in e d tr e m e n d o u s im p e tu s in r ec e n t tim e s. T h e o re tic a l p re d ic tio n s a n d e x p e rim e n ta l re a liz a tio n s o f su ch sy ste m s h a v e g iv e n b irth to a n e w g e n e ra tio n o f m in ia tu riz e d e le ctr o n ic d e v ic e s . O r g a n ic m o le c u le s w ith d e lo c a liz e d ¼ -e le c tro n s sh o w a p ro m isin g fu tu re in th is a sp e c t.T h e lo n g -sta n d in g h isto ry a n d in te re stin g p ro p e rtie s o f tw o iso m e ric o rg a n ic m o le c u le s, n a p h th a le n e a n d a z u le n e , m o tiv a te u s to e x p lo re th e ir e le c tric a l c o n d u c ta n c e p ro p e rty a n d p o ssib le e le c tro n ic d e v ice a p p lic a tio n s th a t e x p lo it th e u n iq u e ch a ra c te ristic s a sso c ia te d w ith th e ir stru c tu ra l a sp e c ts. S in g le m o le c u le o f a z u le n e sh o w s h ig h e r c o n d u c tiv ity th a n n a p h th a le n e . T h e ch a rg e tra n sfe r fro m th e se v e n -m e m b e re d rin g to th e¯v e -m e m b e re d rin g in a z u le n e g iv e s th e sy ste m a ro m a tic sta b ility , m a k in g it d ip o la r. A s a c o n se q u e n c e , th e c o n d u c ta n ce b e c o m e s a sy mm e tric fo r fo rw a rd a n d re v e rse b ia s, o p e n in g a n e ± c ie n t a p p lic a tio n o f a z u le n e a s m o le c u la r re c -ti¯e r in e le c tro n ic d e v ic e fa b ric a tio n .

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Section: Electrical Rectificationmentioning

confidence: 99%

Electrical rectification

Dutta

Pati

2009

Reson

Self Cite

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“…27 Despite quite a large number of theoretical calculations on the inuence of the functional bis-substitution pattern of azulenes on their electronic properties, the experimental investigations have been rather limited. 28,29 Based on theoretical calculations, the 2,6-connected polyazulenes are expected to be most unique compared with other substitution patterns. The p-electrons can easily delocalize along the direction of the dipolar C 2v axis of azulene resulting in a large dipole moment and large hyperpolarizability.…”

Section: Introductionmentioning

confidence: 99%

Impact of 2,6-connectivity in azulene: optical properties and stimuli responsive behavior

2013

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The possible incorporation of the redox active, small donor acceptor molecule azulene as a core structure for potential optoelectronic applications has been evaluated. The synthesis and characterization of different isomers of di(phenylethynyl)azulene 1-4 have been successfully carried out. The photophysical properties as well as their stimuli responsive behavior reflecting their corresponding electronic properties were also investigated. The experimental observations show that 2,6-connection (3) exhibits intense luminescence and shows the strongest stimuli responsive behavior upon acid treatment. DFT calculations of 3 reveal the highest contributions of the alkyne substituents at the 2-and 6-position of the azulene to the ground-and excited state that makes the 2,6-connectivity at azulene a very promising candidate for low band-gap conjugated materials.

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“…In order to construct polyazulenes with the head-to-tail alignment of dipoles, azulene should be functionalized at the 2,6-positions, which are diagonally opposite to each other. This will lead to an alternate arrangement of seven and five-membered rings along the polymer backbone and can facilitate effective electron delocalization along the C 2 axis (C 2v symmetry) passing through 2,6-positions of azulene [23][24][25]. The first chemical synthesis of such polyazulene called poly[2,6aminoazulene] 31 was reported by Luh and co-workers [26] in 2017 and achieved by using the Buchwald-Hartwig reaction protocol (Scheme 7).…”

Section: Poly[26-aminoazulene]mentioning

confidence: 99%

Chemical syntheses and salient features of azulene-containing homo- and copolymers

Shetti¹

2021

Beilstein J. Org. Chem.

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Azulene is a non-alternant, aromatic hydrocarbon with many exciting characteristics such as having a dipole moment, bright color, stimuli responsiveness, anti-Kasha photophysics, and a small HOMO–LUMO gap when compared to its isomer, naphthalene. These properties make azulene-containing polymers an intriguing entity in the field of functional polymers, especially for organic electronic applications like organic field-effect transistors (OFET) and photovoltaic (PV) cells. Since azulene has a fused five and seven-membered ring structure, it can be incorporated onto the polymer backbone through either of these rings or by involving both the rings. These azulene-connection patterns can influence the properties of the resulting polymers and the chemical synthesis in comparison to the electrochemical synthesis can be advantageous in obtaining desired patterns of substitution. Hence, this review article presents a comprehensive overview of the developments that have taken place in the last three decades in the field of chemical syntheses of azulene-containing homo- and copolymers, including brief descriptions of their key properties.

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Comparative study of electron conduction in azulene and naphthalene

Cited by 21 publications

References 27 publications

Electrical rectification

Electrical rectification

Impact of 2,6-connectivity in azulene: optical properties and stimuli responsive behavior

Chemical syntheses and salient features of azulene-containing homo- and copolymers

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