Tuning the structural and spectroscopic properties of donor–acceptor–donor oligomers <i>via</i> mutual X-bonding, H-bonding, and π–π interactions

Weldeab, Asmerom O.; Steen, April E.; Starkenburg, Daken J.; Williams, Jon Steven Dal; Abboud, Khalil A.; Xue, Jiangeng; Hammer, Nathan I.; Castellano, Ronald K.; Watkins, Davita L.

doi:10.1039/c8tc00074c

Cited by 18 publications

(20 citation statements)

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“…Noteworthy are the applications of halogen bonding interactions in materials research and engineering [22][23][24]. We, like others, have shown the impact of halogen bonding in optoelectronic and semiconducting materials [25][26][27][28][29]. Because of its synthetic accessibility, one of the most common building blocks used in the development of organic semiconducting materials is the sulfur-containing heterocycle thiophene [30].…”

Section: Introductionmentioning

confidence: 99%

A Raman Spectroscopic and Computational Study of New Aromatic Pyrimidine-Based Halogen Bond Acceptors

et al. 2019

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Two new aromatic pyrimidine-based derivatives designed specifically for halogen bond directed self-assembly are investigated through a combination of high-resolution Raman spectroscopy, X-ray crystallography, and computational quantum chemistry. The vibrational frequencies of these new molecular building blocks, pyrimidine capped with furan (PrmF) and thiophene (PrmT), are compared to those previously assigned for pyrimidine (Prm). The modifications affect only a select few of the normal modes of Prm, most noticeably its signature ring breathing mode, ν1. Structural analyses afforded by X-ray crystallography, and computed interaction energies from density functional theory computations indicate that, although weak hydrogen bonding (C–H···O or C–H···N interactions) is present in these pyrimidine-based solid-state co-crystals, halogen bonding and π-stacking interactions play more dominant roles in driving their molecular-assembly.

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Section: Introductionmentioning

confidence: 99%

A Raman Spectroscopic and Computational Study of New Aromatic Pyrimidine-Based Halogen Bond Acceptors

et al. 2019

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“…One route to modified properties is the formation of multicomponent complexes, where the introduction of a second molecule into the crystal lattice can facilitate the engineering of solid-state forms with significantly different properties. [16][17][18] In this work, we sought to develop switchable materials by creating and switching between neutral cocrystals and ionic salts. In cocrystals, both components are formally neutral and typically interact through designable intermolecular interactions such as hydrogen or halogen bonding.…”

Section: Introductionmentioning

confidence: 99%

Living in the salt-cocrystal continuum: indecisive organic complexes with thermochromic behaviour

et al. 2019

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“…Directionality of halogen bonding has been recently exploited to engineer the crystalline properties of π‐conjugated systems [83] . Towards this direction, Castellano, Watkins and co‐workers designed an interesting ditopic XB‐acceptor ( DAD‐XB‐Boc ) comprising of a C 2 ‐symmetric pyridyl thiophene‐based donor‐acceptor‐donor (DAD) motif (Figure 16A), which upon co‐crystallization with DITFB produced 2D self‐assembled structures by concomitant X‐bonding and π‐π interactions [84] . Red shifted absorption and emission spectra in the co‐assembly indicates the conformational changes via halogen bonding in the acceptor.…”

Section: Halogen Bonded Supramolecular Polymers and Materialsmentioning

confidence: 99%

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

Biswas

Das

2021

ChemNanoMat

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Polymers have long been known to us for their versatile utility in our daily lives. With many years of successful advancement in controlled polymer synthesis and supramolecular chemistry, currently an amalgamation of these two fields is becoming increasingly important for generating modern‐day emerging polymeric materials. Hydrogen bonding and other noncovalent interactions like π‐stacking, host‐guest interaction, electrostatic interaction, metal‐ligand coordination have been explored much to this context, unlike the recently emerged halogen bonding, which indeed shows advantageous features like superior hydrophobicity, directionality and polar solvent resistance compared to ubiquitous hydrogen bonding. Hence, rendering these properties of halogen bonding into polymeric domain for generating functional materials for application in advance nanotechnologies is highly desirable. In the recent years, substantial progress has been made in fulfilling this challenging goal. This is evident from the escalating number of scientific publications in this research area every year. In this minireview, we have summarized the most recent developments in the field of halogen bonded polymeric assemblies and supramolecular polymers and discussed them in the context of their emerging materials properties and functions. Emphasis is given on highlighting various design criteria adopted in crystal engineering, covalent and supramolecular polymers in the past five years for constructing diverse organic functional materials, viz. liquid crystals, photoresponsive and photochromic materials, biomaterials and gels, self‐healing materials and many others by virtue of this highly directional supramolecular tool. In conclusion, a brief perspective on the advantages, challenges and future prospects in this rapidly growing field of research is discussed.

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Tuning the structural and spectroscopic properties of donor–acceptor–donor oligomers via mutual X-bonding, H-bonding, and π–π interactions

Abstract: Presented are design principles for the combinatory usage of HB, XB, and π–π interactions to enhance solid-state properties essential for optoelectronic device application.

Cited by 18 publications

References 50 publications

A Raman Spectroscopic and Computational Study of New Aromatic Pyrimidine-Based Halogen Bond Acceptors

A Raman Spectroscopic and Computational Study of New Aromatic Pyrimidine-Based Halogen Bond Acceptors

Living in the salt-cocrystal continuum: indecisive organic complexes with thermochromic behaviour

Recent Developments in Polymeric Assemblies and Functional Materials by Halogen Bonding

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